Dimethyl Sulfoxide → N-[(1-Methyl-1H-pyrrol-2-yl)methyl]-10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2246842Notes

Reaction equation

HRID 2246842 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[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:34])=[C:23]([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].[CH3:38][N:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][NH2:45].CS(C)=O.C(N(CC)CC)C>C(#N)C.ClCCl.C(OCC)(=O)C>[CH3:38][N:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][NH:45][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[C:28]([CH3:34])=[CH:29][CH:30]=[CH:31][C:32]=4[CH3:33])=[C:23]([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]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 2776207(1-methyl-1H-pyrrol-2-yl)methanamineHCID 686871492,2,2-trichloro-1-{10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 11999854N-[(1-Methyl-1H-pyrrol-2-yl)methyl]-10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to procedure of Example 2 starting from 2,2,2-trichloro-1-{10-[(2,2′,6′-trimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 3 (1.4 g, 2.5 mmole), (1-methyl-1H-pyrrol-2-yl)methylamine (0.234 g, 2.1 mmole), dimethylsulfoxide (0.822 g, 10.5 mmole) and triethyl amine (0.470 g, 4.6 mmole) in 15 mL of acetonitrile, Flash chromatography of the residue on silica gel Merck-60 (0-25% ethyl acetate in dichloromethane) gave a foam (0.924 g) which solidified upon treatment with ethyl acetate/hexane/dichloromethane, mp. 222-224° C.

Sources & evidence

ORD record
ord-67bf773f69214466a44626c66538ef66
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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