4-(2-Methanesulfonylethyl)aniline → N5-{2-[4-(2-Methanesulfonyl-ethyl)-phenylamino]-pyrimidin-4-yl}-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine hydrochloride

HRID 1391598Notes

Reaction equation

HRID 1391598 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][CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH3:18])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:29][S:30]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:32])=[O:31]>>[ClH:1].[CH3:29][S:30]([CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][C:2]2[N:7]=[C:6]([N:8]([CH3:28])[C:9]3[CH:27]=[CH:26][C:12]4[N:13]([CH3:25])[C:14]([NH:16][CH:17]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH3:18])=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:39][CH:40]=1)(=[O:31])=[O:32]

Participants

3

Reactant 2

HCID 202942424-(2-Methanesulfonylethyl)anilineHCID 59674124N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine

Product 1

HCID 69360339N5-{2-[4-(2-Methanesulfonyl-ethyl)-phenylamino]-pyrimidin-4-yl}-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine hydrochloride

Procedure

The title compound was prepared following the procedure of example two with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 4-(2-methanesulfonyl-ethyl)-phenylamine (50 mg, 0.25 mmol) as a white solid (81 mg, 55%). 1H NMR (300 MHz, d6-DMSO) δ 10.09 (s, 1H), 8.87 (s, 1H), 7.84 (d, J=6.9 Hz, 1H), 7.48-7.61 (m, 5H), 7.36-7.40 (m, 3H), 7.20-7.31 (m, 4H), 5.82 (d, J=5.7 Hz, 1H), 5.09 (m, 1H), 3.74 (s, 3H), 3.47 (s, 3H), 3.37-3.42 (M, 2H), 2.94-2.99 (M, 5H), 1.63 (d, J=6.6 Hz, 3H). MS (ESI) m/z=556 [M+H]+.

Sources & evidence

ORD record
ord-096bfa365a3c4625b772ca7954aacc8e
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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