4-Amino-N-methylbenzeneethanesulfonamide → 2-[4-(4-{[2-(4-Fluoro-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-phenyl]-ethanesulfonic acid methylamide hydrochloride

HRID 1391565Notes

Reaction equation

HRID 1391565 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:28])[C:9]2[CH:27]=[CH:26][C:12]3[N:13]([CH3:25])[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:29][NH:30][S:31]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)(=[O:33])=[O:32]>>[ClH:1].[CH3:29][NH:30][S:31]([CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([NH:42][C:2]2[N:7]=[C:6]([N:8]([C:9]3[CH:27]=[CH:26][C:12]4[N:13]([CH3:25])[C:14]([NH:16][CH2:17][C:18]5[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=5)=[N:15][C:11]=4[CH:10]=3)[CH3:28])[CH:5]=[CH:4][N:3]=2)=[CH:40][CH:41]=1)(=[O:32])=[O:33]

Participants

3

Reactant 2

HCID 134757684-Amino-N-methylbenzeneethanesulfonamideHCID 59674181N5-(2-chloro-pyrimidin-4-yl)-N2-(4-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine

Product 1

HCID 101969112-[4-(4-{[2-(4-Fluoro-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-phenyl]-ethanesulfonic acid methylamide hydrochlorideYield 59%

Procedure

The title compound was prepared following the procedure of example two with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (99 mg, 0.25 mmol) and 2-(4-amino-phenyl)-ethanesulfonic acid methylamide (54 mg, 0.25 mmol) to give the desired product as a white solid (90 mg, 59%). 1H NMR (300 MHz, d6-DMSO) δ 9.04 (s, 1H), 7.68-7.75 (m, 3H), 7.41-7.46 (m, 3H), 7.23 (d, J=8.1 Hz, 1H), 7.08-7.17 (m, 4H), 6.94 (q, J=5.1 Hz, 1H), 6.83 (dd, J=8.1 and 1.5 Hz, 1H), 5.59 (d, J=6.0 Hz, 1H), 4.57 (d, J=5.4 Hz, 2H), 3.56 (s, 3H), 3.41 (s, 3H), 3.20-3.26 (m, 2H), 2.83-2.88 (m, 2H), 2.59 (d, J=5.1 Hz, 3H). MS (ESI) m/z=575 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-781a773a8e0b4948881bd81d96b5dc9e
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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