1-(4-Aminophenyl)methanesulfonamide → (4-Methoxy-phenyl)-(1-methyl-5-{methyl-[2-(4-sulfamoylmethyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester

HRID 1391609Notes

Reaction equation

HRID 1391609 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([C:16]1[N:20]([CH3:21])[C:19]2[CH:22]=[CH:23][C:24]([N:26]([C:28]3[CH:33]=[CH:32][N:31]=[C:30](Cl)[N:29]=3)[CH3:27])=[CH:25][C:18]=2[N:17]=1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][S:44]([NH2:47])(=[O:46])=[O:45])=[CH:39][CH:38]=1>>[C:1]([O:5][C:6](=[O:35])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:16]1[N:20]([CH3:21])[C:19]2[CH:22]=[CH:23][C:24]([N:26]([CH3:27])[C:28]3[CH:33]=[CH:32][N:31]=[C:30]([NH:36][C:37]4[CH:42]=[CH:41][C:40]([CH2:43][S:44](=[O:46])(=[O:45])[NH2:47])=[CH:39][CH:38]=4)[N:29]=3)=[CH:25][C:18]=2[N:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 108214071-(4-Aminophenyl)methanesulfonamideHCID 59674233{5-[(2-Chloro-pyrimidin-4-yl)-methyl-amino]-1-methyl-1H-benzoimidazol-2-yl}-(4-methoxy-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 10290407(4-Methoxy-phenyl)-(1-methyl-5-{methyl-[2-(4-sulfamoylmethyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester

Procedure

The title compound was prepared following the procedure of example 78 using {5-[(2-Chloro-pyrimidin-4-yl)-methyl-amino]-1-methyl-1H-benzoimidazol-2-yl}-(4-methoxy-phenyl)-carbamic acid tert-butyl ester (100 mg, 0.20 mmol) and (4-amino-phenyl)-methanesulfonamide (37 mg, 0.20 mmol) to give the desired product as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 9.20 (s, 1H), 7.81 (d, J=6.0 Hz, 1H), 7.65-7.73 (m, 3H), 7.54 (d, J=1.8 Hz, 1H), 7.34 (d, J=8.7 Hz, 2H), 7.24 (dd, J=8.4 and 1.8 Hz, 1H), 7.16 (d, J=8.4 Hz, 2H), 6.97 (d, J=9.0 Hz, 2H), 6.75 (s, 2H), 5.69 (d, J=6.0 Hz, 1H), 4.14 (s, 2H), 3.78 (s, 3H), 3.74 (s, 3H), 3.46 (s, 3H), 1.41 (s, 9H). MS (ESI) m/z=645 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-065f41a7e6554b929776161f90cf62f8
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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