Methylamine tetrahydrofuran → tert-Butyl methyl{[1-({3-[(methylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}carbamate

HRID 554359Notes

Reaction equation

HRID 554359 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=O)(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][NH2:35].O1CCCC1>>[CH3:9][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:14]([S:16]([C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22]([NH:35][CH3:34])=[O:24])[CH:20]=2)(=[O:18])=[O:17])[CH:15]=1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 66615946Methylamine tetrahydrofuranHCID 669249903-[(4-{[(tert-Butoxycarbonyl)(methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoic acid

Product 1

HCID 66925073tert-Butyl methyl{[1-({3-[(methylamino)carbonyl]phenyl}sulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}carbamateYield 64%

Procedure

Using 3-[(4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoic acid (150 mg) and 2 mol/L methylamine-tetrahydrofuran solution (5 mL), a procedure as in Reference Example 284 was performed to give the title compound as a colorless oil (yield 99 mg, 64%).

Sources & evidence

ORD record
ord-7f5cd9ac133a473f891e50f6e4b7e04e
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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