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

HRID 347648Notes

Reaction equation

HRID 347648 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].[CH2:13]([N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][CH2:18][CH2:17][CH2:16]1)[CH3:14]>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:19]2[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][CH2:18]2)=[O:9])=[CH:5][C:4]=1[CH3:12])#[N:2]

Participants

3

Reactant 2

HCID 102410994-Cyano-3-methylbenzoic acidHCID 196082311-Ethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Product 1

HCID 210832441-(4-Cyano-3-methylbenzoyl)-5-ethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Procedure

The carboxylic acid from Example C (0.53 g, 3.29 mmol) was reacted with 1-ethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 23B (0.514 g, 2.92 mmol) according to the procedure in Example 1A. The product was purified by flash chromatography on silica (eluant EtOAc:pet. ether 60:40); yield 0.55 g (59%).

Workup

  1. customThe product was purified by flash chromatography on silica (eluant EtOAc:pet. ether 60:40)

Sources & evidence

ORD record
ord-4d014085568e4a84a61be549aaa5a1fe
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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