1-Phenethylamine → 10-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-YL)carbonyl]-N-(1-phenylethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639257Notes

Reaction equation

HRID 639257 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[C:23]([O:34][CH3:35])[CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[C:38]1([CH:44]([NH2:46])[CH3:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH3:35][O:34][C:23]1[CH:22]=[C:21]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:46][CH:44]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH3:45])=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])[CH:26]=[CH:25][C:24]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

3

Reactant 2

HCID 74081-PhenethylamineHCID 160388252,2,2-Trichloro-1-{10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 6867941810-[(2-Methoxy-2'-methyl-1,1'-biphenyl-4-YL)carbonyl]-N-(1-phenylethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

Procedure

The title compound was prepared in the manner of Example 36 from 2,2,2-trichloro-1-{10-[(2-methoxy-2′-methyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 35 and (±)-1-phenylethylamine. Purification was performed using HPLC with a normal phase column by eluting with a two phase solvent system (A=hexane, B=dichloromethane/methanol, 4:1) that gave the title compound in 63% yield, m.p. 211° C. MS [(+)ESI, m/z]: 554 [M+H]+ Anal. Calcd for C36H33N3O3: C, 77.81; H, 5.99; N, 7.56. Found: C, 77.65; H, 6.01; N, 7.45.

Workup

  1. customPurification
  2. washby eluting with a two phase solvent system (A=hexane, B=dichloromethane/methanol, 4:1) that

Sources & evidence

ORD record
ord-cf3c0f01a4c046e182c0e1aabecb27b8
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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