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Tetrahedron Letters

Volumn 44, Issue 48, 2003, Pages 8661-8663

A concise synthesis of ortho-substituted aryl-acrylamides - Potent activators of soluble guanylyl cyclase

(4) Zhang, Henry Q a Xia, Zhiren a Kolasa, Teodozyj a Dinges, Jurgen a

a ABBOTT LABORATORIES (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; ALDEHYDE; AMIDE; GUANYLATE CYCLASE ACTIVATOR; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DRUG POTENCY; DRUG SYNTHESIS; FILTRATION; GAS CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; STRUCTURE ACTIVITY RELATION;

EID: 0142215706 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/j.tetlet.2003.09.161 Document Type: Article

Times cited : (11)

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16
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- 3b: A mixture of diethylphosphonoacetic acid (620 mg, 3.0 mmol), N-cyclohexylcarbodimide, N′-methyl polystyrene (5.0 g, 9.6 mmol) and HOBt (450 mg, 3.3 mmol) in N,N-dimethylacetamide/dichloromethane (1:1, 60 mL) was shaken at room temperature for 15 min. 4-(Dimethylamino)butyl amine (570 mg, 4. 9 mmol) in N,N-dimethylacetamide/dichloromethane (1:1, 10 mL) was added and the resulting mixture was shaken at room temperature for 18 h. Trisamine polystyrene (5.0 g, 20 mmol) was added and the resulting mixture was shaken at room temperature for 6 h. The reaction solution was collected by filtration. The resin was washed with dichloromethane (2×10 mL). The combined filtrate was concentrated in vacuo. The residue 0.89 g (100%) was used without purification.
- +.

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19
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- 3a (28 mg, 0.1 mmol) in anhydrous THF (Aldrich, 1.5 mL) was added LDA (Aldrich, 2.0 M in heptane/THF/ethylbenzne, 0.25 mL, 0.5 mmol) at room temperature. After 30 min, 2-(3-chlorophenylthio)benzaldehyde (20 mg, 0.08 mmol) in anhydrous THF (0.75 mL) was added. The reaction mixture was stirred at room temperature for 1 h and quenched with water (0.3 mL). The reaction mixture was concentrated. The residue was purified by preparative HPLC on a Waters Symmetry C8 column (25×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile: 0.1% aqueous TFA over about 8 min (10 min run time) at a flow rate of 40 ml/min to provide 21 mg (54%) of the desired product, 4a (Table 1, entry 4) as a trifluoroacetic acid salt.
- +.

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