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

HRID 1391594Notes

Reaction equation

HRID 1391594 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:29])[C:9]2[CH:28]=[CH:27][C:12]3[N:13]([CH3:26])[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][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].[CH3:30][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]([CH3:29])[C:9]3[CH:28]=[CH:27][C:12]4[N:13]([CH3:26])[C:14]([NH:16][CH2:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=5)=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:40][CH:41]=1)(=[O:32])=[O:33]

Participants

3

Reactant 2

HCID 202942424-(2-Methanesulfonylethyl)anilineHCID 59674096HCID 59674096, compound

Product 1

HCID 10290036N5-{2-[4-(2-Methanesulfonyl-ethyl)-phenylamino]-pyrimidin-4-yl}-N2-(4-methoxy-benzyl)-1,N5-dimethyl-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)-N2-(4-methoxy-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (82 mg, 0.20 mmol) and 4-(2-Methanesulfonyl-ethyl)-phenylamine (40 mg, 0.20 mmol) as a white solid (57 mg, 47%). 1H NMR (300 MHz, d6-DMSO) δ 9.28 (s, 1H), 7.78 (d, J=6.0 Hz, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.34-7.38 (m, 3H), 7.13-7.18 (m, 3H), 6.94 (d, J=8.4 Hz, 1H), 6.89 (d, J=8.7 Hz, 2H), 5.66 (d, J=6.0 Hz, 1H), 4.57 (d, J=5.4 Hz, 2H), 3.72 (s, 3H), 3.62 (s, 3H), 3.43 (s, 3H), 3.35-3.43 (m, 2H), 2.96 (s, 3H), 2.90-2.96 (m, 2H). MS (ESI) m/z=572 [M+H]+.

Sources & evidence

ORD record
ord-725819a8b7c14eb6979d28e5c29a9b2a
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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