Solid-phase synthesis of 1,5-benzodiazepin-2-ones

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8397-8400

  Schwarz, Matthias K ^a   Tumelty, David ^a   Gallop, Mark A ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BENZODIAZEPIN 2 ONE DERIVATIVE; BENZODIAZEPIN 2 ONE DERIVATIVE; BETA AMINO ACID; NITROBENZOIC ACID DERIVATIVE; RESIN; UNCLASSIFIED DRUG;

ALKYLATION; DRUG SYNTHESIS; REDUCTION; REVIEW; SOLID PHASE EXTRACTION;

EID: 0032511925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01956-X     Document Type: Article

References (19)

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4. nd Canadian Conference of Combinatorial Chemistry, Montreal, Canada, Oct. 6-7, 1997. Described were solid-phase syntheses of 1,5-benzothiazepin-4-ones, 1,6-benzothiazocin-5-ones, 1,5-benzodiazepin-2-ones, 4-alkoxy-1,4-thiazin-3-ones, quinoxalin-2-ones, and of a thieno-thiazepine.
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17. 2O (2x), and dried in vacuo. General procedure for N(5)-alkylation: To 150 mg of resin 7 was added 2 ml of a 2M solution of the alkyl halide in DMF, and the reaction was allowed to proceed at 55-60°C for 3.5 days. After removal of the supernatant, the resin was extensively washed with DMF (5x), DCM (3x), MeOH (3x), DCM (2x), DMF (3x), DCM (3x), and dried in vacuo. 12. The difference between the values obtained for crude and isolated yields are due to the presence of PEG residues in the crude samples (resin "bleeding"), as well as to losses encountered during RP-HPLC purification of the compounds.
18. +).
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