4-Cyano-3-methylbenzoic acid → 1-(4-Cyano-3-methylbenzoyl)-5-(3-pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 347642Notes

Reaction equation

HRID 347642 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].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][CH2:23][CH2:22][CH2:21]2)[CH:14]=1>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:24]2[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:20]([CH2:19][C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)[CH2:21][CH2:22][CH2:23]2)=[O:9])=[CH:5][C:4]=1[CH3:12])#[N:2]

Participants

3

Reactant 2

HCID 102410994-Cyano-3-methylbenzoic acidHCID 107763951-(3-Pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Product 1

HCID 210832431-(4-Cyano-3-methylbenzoyl)-5-(3-pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Procedure

The carboxylic acid from Example C (0.31 g, 1.93 mmol) was reacted with 1-(3-pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 16A (0.39 g, 1.61 mmol) according to the procedure in Example 1A. The product was purified by flash chromatography on silica (eluant EtOAc); yield 0.28 g (45%).

Workup

  1. customThe product was purified by flash chromatography on silica (eluant EtOAc)

Sources & evidence

ORD record
ord-26687def1709462bb65bc7ebd78fe4a3
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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