2,3,4,5-tetrahydro-1H-1,5-benzodiazepine → 1-(4-Cyano-3-methylbenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 347640Notes

Reaction equation

HRID 347640 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[CH3:12])#[N:2].[NH:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][CH2:16][CH2:15][CH2:14]1>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][CH2:16][CH2:15][CH2:14]2)=[O:9])=[CH:5][C:4]=1[CH3:12])#[N:2]

Participants

3

Reactant 2

HCID 5771922,3,4,5-tetrahydro-1H-1,5-benzodiazepineHCID 102410994-Cyano-3-methylbenzoic acid

Product 1

HCID 210832411-(4-Cyano-3-methylbenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Procedure

The carboxylic acid from Example C (0.65 g, 4.03 mmol) was reacted with 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 15A (0.50 g, 3.36 mmol) according to the procedure in Example 1A. The product was purified by flash chromatography on silica (eluant EtOAc:pet. ether 50:50); yield 0.36 g (37%).

Workup

  1. customThe product was purified by flash chromatography on silica (eluant EtOAc:pet. ether 50:50)

Sources & evidence

ORD record
ord-6a78b70ee21140fabd6dbbdd5bbe8820
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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