Water → N-[2-(4-Hydroxyphenyl)ethyl]-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 639268Notes

Reaction equation

HRID 639268 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:9]2[CH2:10][C:11]3[CH:35]=[CH:34][CH:33]=[CH:32][C:12]=3[N:13]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[C:19]([CH3:31])[CH:18]=3)=[O:16])[CH2:14][C:8]2=[CH:7][CH:6]=1)=[O:4].[NH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1.O>CS(C)=O>[OH:47][C:44]1[CH:45]=[CH:46][C:41]([CH2:40][CH2:39][NH:38][C:3]([C:5]2[N:9]3[C:8]([CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[O:29][CH3:30])=[C:19]([CH3:31])[CH:18]=4)=[O:16])[C:12]4[CH:32]=[CH:33][CH:34]=[CH:35][C:11]=4[CH2:10]3)=[CH:7][CH:6]=2)=[O:4])=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5610TyramineHCID 219479472,2,2-trichloro-1-[10-(2'-methoxy-2-methyl-biphenyl-4-carbonyl)-10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-ethanone

Product 1

HCID 16039218N-[2-(4-Hydroxyphenyl)ethyl]-10-[(2'-methoxy-2-methyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideYield 94.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 2,2,2-trichloro-1-[10-(2′-methoxy-2-methyl-biphenyl-4-carbonyl)-10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-ethanone of step D (0.175 g; 0.316 mmol) and tyramine (0.087 g; 0.632 mmol) were stirred in 3 mL of dimethylsulfoxide under a nitrogen atmosphere at 80° C. for 18 hours. The solution was cooled and 15 mL water were added. The resulting solid was filtered and dried to provide the title compound (0.171 g, 94%), m.p. 138-147° C. MS [(+)ESI, m/z]: 572.2 [M+H]+

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-8aeb5877008a458fa27c6b600201d6df
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

Loading…