3-(Methanesulfonylmethyl)aniline → (5-{[2-(3-Methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-methyl-amino}-1-methyl-1H-benzoimidazol-2-yl)-(4-methoxy-phenyl)-carbamic acid tert-butyl ester

HRID 1391610Notes

Reaction equation

HRID 1391610 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].[CH3:36][S:37]([CH2:40][C:41]1[CH:42]=[C:43]([NH2:47])[CH:44]=[CH:45][CH:46]=1)(=[O:39])=[O:38]>>[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]([NH:47][C:43]4[CH:44]=[CH:45][CH:46]=[C:41]([CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[CH:42]=4)[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]

Participants

3

Reactant 2

HCID 219563393-(Methanesulfonylmethyl)anilineHCID 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 59674172(5-{[2-(3-Methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-methyl-amino}-1-methyl-1H-benzoimidazol-2-yl)-(4-methoxy-phenyl)-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 3-methanesulfonylmethyl-phenylamine (37 mg, 0.20 mmol) to give the desired product as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 9.44 (s, 1H), 7.80-7.82 (m, 2H), 7.63-7.70 (M, 2H), 7.56 (d, J=1.5 Hz, 1H), 7.34 (d, J=8.7 Hz, 2H), 7.25 (dd, J=8.6 and 1.2 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 6.94 (d, J=9.0 Hz, 2H), 5.75 (d, J=6.0 Hz, 1H), 4.34 (s, 2H), 3.79 (s, 3H), 3.74 (s, 3H), 3.47 (s, 3H), 2.89 (s, 3H), 1.41 (s, 9H). MS (ESI) m/z=644 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0b104134e93149c9892b1f0824ee67b9
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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