Dimethyl Sulfoxide → HCID 11998033, compound

HRID 2246841Notes

Reaction equation

HRID 2246841 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].[CH2:37]([N:44]1[CH2:49][CH2:48][O:47][CH:46](NC)[CH2:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CS(C)=O.[CH2:56]([N:58](CC)CC)C>C(#N)C>[CH2:37]([N:44]1[CH2:49][CH2:48][O:47][CH:46]([CH2:56][NH:58][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH3:34])=[CH:25][CH:26]=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])[CH2:45]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=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 21104591HCID 21104591, compound

Product 1

HCID 11998033HCID 11998033, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to the procedure of Example 2 starting 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 of Example 1 (0.619 g, 1.15 mmole), (4-benzyl-1,4-oxazinan-2-yl)-methylamine (01.97 g, 0.955 mmole), dimethylsulfoxide (0.374 g, 4.8 mmole), and triethylamine (0.213 g, 2.1 mmole) in 15 mL of acetonitrile. The residue was adsorbed on silica Merck-60 and purified by flash chromatography (0-75% ethyl acetate in dichloromethane) to provide an off white solid (0.241 g), m.p. 180-182° C.

Workup

  1. custompurified by flash chromatography (0-75% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-febe4db4aaa14aedb49043f1deeaa8e9
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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