-
1
-
-
0019782980
-
-
Vale, W.; Spiess, J.; Rivier, C. Science 1981, 213, 1394-1397
-
(1981)
Science
, vol.213
, pp. 1394-1397
-
-
Vale, W.1
Spiess, J.2
Rivier, C.3
-
6
-
-
79952835056
-
-
Gilligan, P. J.; Clarke, T.; He, L.; Lelas, S.; Li, Y.-W.; Heman, K.; Fitzgerald, L.; Miller, K.; Zhang, G.; Marshall, A.; Krause, C.; McElroy, J. F.; Ward, K.; Zeller, K.; Wong, H.; Bai, S.; Saye, J.; Grossman, S.; Zaczek, R.; Arneric, S. P.; Hartig, P.; Robertson, D.; Trainor, G. J. Med. Chem. 2009, 52, 3804-3092
-
(2009)
J. Med. Chem.
, vol.52
, pp. 3804-3092
-
-
Gilligan, P.J.1
Clarke, T.2
He, L.3
Lelas, S.4
Li, Y.-W.5
Heman, K.6
Fitzgerald, L.7
Miller, K.8
Zhang, G.9
Marshall, A.10
Krause, C.11
McElroy, J.F.12
Ward, K.13
Zeller, K.14
Wong, H.15
Bai, S.16
Saye, J.17
Grossman, S.18
Zaczek, R.19
Arneric, S.P.20
Hartig, P.21
Robertson, D.22
Trainor, G.23
more..
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7
-
-
65649118273
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-
references cited therein
-
Gilligan, P. J.; He, L.; Clarke, T.; Tivitmahaisoon, P.; Lelas, S.; Li, Y.-W.; Heman, K.; Fitzgerald, L.; Miller, K.; Zhang, G.; Marshall, A.; Krause, C.; McElroy, J.; Ward, K.; Shen, H.; Wong, H.; Grossman, S.; Nemeth, G.; Zaczek, R.; Arneric, S. P.; Hartig, P.; Robertson, D. W.; Trainor, G. J. Med. Chem. 2009, 52, 3073-3083 and references cited therein
-
(2009)
J. Med. Chem.
, vol.52
, pp. 3073-3083
-
-
Gilligan, P.J.1
He, L.2
Clarke, T.3
Tivitmahaisoon, P.4
Lelas, S.5
Li, Y.-W.6
Heman, K.7
Fitzgerald, L.8
Miller, K.9
Zhang, G.10
Marshall, A.11
Krause, C.12
McElroy, J.13
Ward, K.14
Shen, H.15
Wong, H.16
Grossman, S.17
Nemeth, G.18
Zaczek, R.19
Arneric, S.P.20
Hartig, P.21
Robertson, D.W.22
Trainor, G.23
more..
-
8
-
-
79952846818
-
-
PCT Int. Appl. WO/2002/072202.
-
Gilligan, P. J. PCT Int. Appl. WO/2002/072202, 2002.
-
(2002)
-
-
Gilligan, P.J.1
-
9
-
-
18344405707
-
-
He, L.; Gilligan, P. J.; Zaczek, R.; Fitzgerald, L. W.; McElroy, J.; Shen, H-S.L.; Saye, J. A.; Kalin, N. H.; Shelton, S.; Christ, D.; Trainor, G.; Hartig, P. J. Med. Chem. 2000, 43, 449-456
-
(2000)
J. Med. Chem.
, vol.43
, pp. 449-456
-
-
He, L.1
Gilligan, P.J.2
Zaczek, R.3
Fitzgerald, L.W.4
McElroy, J.5
Shen, H.-S.L.6
Saye, J.A.7
Kalin, N.H.8
Shelton, S.9
Christ, D.10
Trainor, G.11
Hartig, P.12
-
10
-
-
0028361735
-
-
Gray, M. A.; Konopski, L.; Langlois, Y. Synth. Commun. 1994, 24, 1367-1379
-
(1994)
Synth. Commun.
, vol.24
, pp. 1367-1379
-
-
Gray, M.A.1
Konopski, L.2
Langlois, Y.3
-
11
-
-
0042351912
-
-
Kochetkov, N. K.; Sokolov, S. D.; Vagurtova, N. M. Zh. Obshch. Khim. 1961, 31, 2326-2333
-
(1961)
Zh. Obshch. Khim.
, vol.31
, pp. 2326-2333
-
-
Kochetkov, N.K.1
Sokolov, S.D.2
Vagurtova, N.M.3
-
12
-
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79952826555
-
-
U.S. Pat. 6,562,965.
-
Zhou, J.; Oh, L. M.; Ma, P. U.S. Pat. 6,562,965, 2003.
-
(2003)
-
-
Zhou, J.1
Oh, L.M.2
Ma, P.3
-
13
-
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79952832834
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United States Environmental Protection Agency, (created in April 1992; revised in January 2000; updated in November 2007); (accessed September 9, 2010)
-
Hydrazine Hazard Summary; United States Environmental Protection Agency, (created in April 1992; revised in January 2000; updated in November 2007) 2007; http://www.epa.gov/ttn/atw/hlthef/hydrazin.html (accessed September 9, 2010).
-
(2007)
Hydrazine Hazard Summary
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-
-
14
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79952849717
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JP 2001302658
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The pyridyl starting material was obtained from commercial sources or by custom synthesis, see: Miyata, H.; Oki, K.; Morikawa, K. JP 2001302658, 2001.
-
(2001)
-
-
Miyata, H.1
Oki, K.2
Morikawa, K.3
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15
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79952832624
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CN 1088574
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Yu, Z. CN 1088574, 1994
-
(1994)
-
-
Yu, Z.1
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16
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0010149263
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-
Nishida, A.; Shirakawa, S.; Harada, T.; Fujisaki, S.; Kajigaeshi, S. Technol. Rep. Yamaguchi Univ. 1988, 4, 145-50
-
(1988)
Technol. Rep. Yamaguchi Univ.
, vol.4
, pp. 145-50
-
-
Nishida, A.1
Shirakawa, S.2
Harada, T.3
Fujisaki, S.4
Kajigaeshi, S.5
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17
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0017785206
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-
Nagel, D. L.; Kupper, R.; Antonson, K.; Wallcave., L. J. Org. Chem. 1977, 42, 3626-3628
-
(1977)
J. Org. Chem.
, vol.42
, pp. 3626-3628
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-
Nagel, D.L.1
Kupper, R.2
Antonson, K.3
Wallcave, L.4
-
22
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79952846182
-
-
To ensure full dissolution of 16, 4 equiv were necessary
-
To ensure full dissolution of 16, 4 equiv were necessary.
-
-
-
-
23
-
-
79952849318
-
-
2O as solvent did not lead to appreciable levels of conversion.
-
2O as solvent did not lead to appreciable levels of conversion.
-
-
-
-
24
-
-
79952828754
-
-
Pure regioisomers trans - 13a and semicarbazone 13b were isolated and used for characterization. The cis -isomer was not observed.
-
Pure regioisomers trans-13a and semicarbazone 13b were isolated and used for characterization. The cis -isomer was not observed.
-
-
-
-
25
-
-
79952838282
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-
The isomer ratio was estimated by careful solid-state NMR techniques as 13a and 13b were observed to readily interconvert in solution.
-
The isomer ratio was estimated by careful solid-state NMR techniques as 13a and 13b were observed to readily interconvert in solution.
-
-
-
-
26
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-
79952842005
-
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2O prior to the start of the subsequent API step.
-
2O prior to the start of the subsequent API step.
-
-
-
-
27
-
-
79952860725
-
-
2O afforded the monohydrate. Prolonged exposure of anhydrous 10 as a slurry in the presence of water at room temperature did not produce the monohydrate form.
-
2O afforded the monohydrate. Prolonged exposure of anhydrous 10 as a slurry in the presence of water at room temperature did not produce the monohydrate form.
-
-
-
-
28
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-
79952848253
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-
With 1 mol % of DBU, the solubility of 10 is 2 mg/mL whereas with 5 mol % it is 25 mg/mL.
-
With 1 mol % of DBU, the solubility of 10 is 2 mg/mL whereas with 5 mol % it is 25 mg/mL.
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-
-
-
30
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0031523832
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Anderson, N. G.; Ary, T. D.; Berg, J. L.; Bernot, P. J.; Chan, Y. Y.; Chen, C.-K; Davies, M. L.; DiMarco, J. D.; Dennis, R. D.; Deshpande, R. P.; Do, H. D.; Droghini, R.; Early, W. A.; Gougoutas, J. Z.; Grosso, J. A.; Harris, J. C.; Haas, O. W.; Jass, P. A.; Kim, D. H.; Kodersha, G. A.; Kotnis, A. S.; LaJeunesse, J.; Lust, D. A.; Madding, G. D.; Modi, S. P.; Moniot, J. L.; Nguyen, A.; Palaniswamy, V.; Phillipson, D. W.; Simpson, J. H.; Thoraval, D.; Thurston, D. A.; Tse, K.; Polomski, R. E.; Wedding, D. L.; Winter, W. J. Org. Process Res. Dev. 1997, 1, 300-310
-
(1997)
Org. Process Res. Dev.
, vol.1
, pp. 300-310
-
-
Anderson, N.G.1
Ary, T.D.2
Berg, J.L.3
Bernot, P.J.4
Chan, Y.Y.5
Chen, C.-K.6
Davies, M.L.7
Dimarco, J.D.8
Dennis, R.D.9
Deshpande, R.P.10
Do, H.D.11
Droghini, R.12
Early, W.A.13
Gougoutas, J.Z.14
Grosso, J.A.15
Harris, J.C.16
Haas, O.W.17
Jass, P.A.18
Kim, D.H.19
Kodersha, G.A.20
Kotnis, A.S.21
Lajeunesse, J.22
Lust, D.A.23
Madding, G.D.24
Modi, S.P.25
Moniot, J.L.26
Nguyen, A.27
Palaniswamy, V.28
Phillipson, D.W.29
Simpson, J.H.30
Thoraval, D.31
Thurston, D.A.32
Tse, K.33
Polomski, R.E.34
Wedding, D.L.35
Winter, W.J.36
more..
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32
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79952829174
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-
Similar conditions were utilized for a related molecule, see ref 6
-
Similar conditions were utilized for a related molecule, see ref 6.
-
-
-
-
33
-
-
0035615863
-
-
The addition of HCl or LiCl is thought to collapse the intermediate dichlorophosphinate ester, see: Fujino, K.; Takami, H.; Atsumi, T.; Ogasa, T.; Mohri, S.-i; Kasai, M. Org. Process Res. Dev. 2001, 5, 426-433
-
(2001)
Org. Process Res. Dev.
, vol.5
, pp. 426-433
-
-
Fujino, K.1
Takami, H.2
Atsumi, T.3
Ogasa, T.4
Mohri, S.-I.5
Kasai, M.6
-
34
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-
13844255095
-
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Connolly, T. J.; Matchett, M.; Sarma, K. Org. Process Res. Dev. 2005, 9, 80-87
-
(2005)
Org. Process Res. Dev.
, vol.9
, pp. 80-87
-
-
Connolly, T.J.1
Matchett, M.2
Sarma, K.3
-
35
-
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0035615863
-
-
Fujino, K.; Takami, H.; Atsumi, T.; Ogasa, T.; Mohri, S.-i.; Kasai, M. Org. Process Res. Dev. 2001, 5, 426-433
-
(2001)
Org. Process Res. Dev.
, vol.5
, pp. 426-433
-
-
Fujino, K.1
Takami, H.2
Atsumi, T.3
Ogasa, T.4
Mohri, S.-I.5
Kasai, M.6
-
36
-
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79952843742
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-
A similar dimeric impurity has been observed, see ref 20.
-
A similar dimeric impurity has been observed, see ref 20.
-
-
-
-
37
-
-
79952860298
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-
The influence of solvent for the chlorination reaction is under investigation and will be reported in due course
-
The influence of solvent for the chlorination reaction is under investigation and will be reported in due course.
-
-
-
-
38
-
-
79952848894
-
-
Recently, patents reporting the use of DABCO as catalyst were published, see: Aiqing, F. Zhuanli, F. Shuomingshu, G. S., CN 101423498 A 20090506 (CAN 150:563847 AN 2009:561663), 2009.
-
(2009)
CN 101423498 A 20090506 (CAN 150:563847 AN 2009:561663)
-
-
Aiqing, F.1
Zhuanli, F.2
Shuomingshu, G.S.3
-
39
-
-
79952844699
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CN 101445485 A 20090603 (CAN 151:78133 AN 2009:689505).
-
Aiqing, F. Zhuanli, F. Shuomingshu, G. S. CN 101445485 A 20090603 (CAN 151:78133 AN 2009:689505), 2009.
-
(2009)
-
-
Aiqing, F.1
Zhuanli, F.2
Shuomingshu, G.S.3
-
40
-
-
79952820954
-
-
The exact role of DABCO in the catalyzed chlorination is currently under investigation and will be disclosed in due course
-
The exact role of DABCO in the catalyzed chlorination is currently under investigation and will be disclosed in due course.
-
-
-
-
44
-
-
79952834772
-
-
Doronina, S. O.; Gall, A. A.; Shishkin, G. V. Khim. Geterotsikl. Soedin. 1992, 8, 1091-1094
-
(1992)
Khim. Geterotsikl. Soedin.
, vol.8
, pp. 1091-1094
-
-
Doronina, S.O.1
Gall, A.A.2
Shishkin, G.V.3
-
45
-
-
79952850160
-
-
3 was added in 4 min, resulting in an increase of batch temperature from -4 to 3.5 °C with the jacket temperature set to -10 °C.
-
3 was added in 4 min, resulting in an increase of batch temperature from -4 to 3.5 °C with the jacket temperature set to -10 °C.
-
-
-
-
47
-
-
79952822025
-
-
Enamine formation may occur via hydride transfer as described in ref 32 or as shown below
-
Enamine formation may occur via hydride transfer as described in ref 32 or as shown below
-
-
-
|