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

HRID 2244206Notes

Reaction equation

HRID 2244206 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[O:33][CH3:34])=[CH:23][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-].[O:38]([C:45]1[C:50]([CH2:51][NH3+:52])=[CH:49][CH:48]=[CH:47][N:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C.CS(C)=O>C(#N)C>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[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:52][CH2:51][C:50]4[C:45]([O:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)=[N:46][CH:47]=[CH:48][CH:49]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneHCID 866096892-Phenoxy-pyridin-3-ylmethyl-ammonium chloride

Product 1

HCID 1595308210-[(2'-Methoxy-1,1'-biphenyl-4-YL)carbonyl]-N-[(2-phenoxypyridin-3-YL)methyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamideYield 26.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to the procedure of Example 6, Step D, from 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone (0.20 g, 0.379 mmol), 2-phenoxy-pyridin-3-ylmethyl-ammonium chloride (0.192 g, 0.78 mmol), triethylamine (0.112 g, 0.8 mmol), dimethylsulfoxide (0.131 mL, 1.85 mmol), and acetonitrile (5 mL). The crude material was purified by hplc using the following conditions: solvent system, 65:35 acetonitrile:water (0.1% trifluoroacetic acid); Primesphere 10 C18, 250 by 50 mm column; flow rate 100 mL/min) to provide the title compound (0.062 g) as a white solid.

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified by hplc

Sources & evidence

ORD record
ord-cf7ba76a442340059aa3a59af4ea7cde
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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