Triethylamine → N-[4-(Dimethylamino)benzyl]-10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-YL)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639256Notes

Reaction equation

HRID 639256 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].Cl.Cl.[NH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]([CH3:50])[CH3:49])=[CH:44][CH:43]=1.C(N(CC)CC)C>>[CH3:49][N:48]([CH3:50])[C:45]1[CH:46]=[CH:47][C:42]([CH2:41][NH:40][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH3:33])=[C:23]([O:34][CH3:35])[CH:22]=4)=[O:20])[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13]3)=[CH:7][CH:6]=2)=[O:4])=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 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 16038416N-[4-(Dimethylamino)benzyl]-10-[(2-methoxy-2'-methyl-1,1'-biphenyl-4-YL)carbonyl]-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 (4-aminomethylphenyl)-dimethylamine dihydrochloride in the presence of two equivalents of triethylamine. Purification was performed using HPLC with a normal phase column. Elution with a mixture of etoxynonafluorobutane and methanol gave the title compound in 37% yield, m.p. 148-150° C. MS [(+)ESI, m/z]: 585 [M+H]+

Workup

  1. customPurification
  2. washElution
  3. additionwith a mixture of etoxynonafluorobutane and methanol

Sources & evidence

ORD record
ord-4c9b1968ff074e14ba239f5eeba49354
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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