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

HRID 1391625Notes

Reaction equation

HRID 1391625 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:26])[C:9]2[CH:25]=[CH:24][C:12]3[N:13]([CH3:23])[C:14]([NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:27][S:28]([CH:31]([C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH3:32])(=[O:30])=[O:29]>>[ClH:1].[CH:17]1([NH:16][C:14]2[N:13]([CH3:23])[C:12]3[CH:24]=[CH:25][C:9]([N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:39][C:36]5[CH:37]=[CH:38][C:33]([CH:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH3:32])=[CH:34][CH:35]=5)[N:7]=4)[CH3:26])=[CH:10][C:11]=3[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 596741424-(1-Methanesulfonylethyl)anilineHCID 59674146HCID 59674146, compound

Product 1

HCID 86601121N2-Cyclohexyl-N5-{2-[4-(1-methanesulfonyl-ethyl)-phenylamino]-pyrimidin-4-yl}-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine hydrochloride

Procedure

The title compound was prepared following the procedure of example 1 with N5-(2-Chloro-pyrimidin-4-yl)-N2-cyclohexyl-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (74 mg, 0.20 mmol) and 4-(1-methanesulfonyl-ethyl)-phenylamine (40 mg, 0.20 mmol) as a white solid (104 mg, 91%). 1H NMR (300 MHz, D6-DMSO) δ 9.34 (s, 1H), 7.85 (d, J=6.0 Hz, 1H), 7.71 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.1 Hz, 1H), 7.22-7.26 (m, 3H), 7.08 (d, J=8.1 Hz, 1H), 5.76 (d, J=6.0 Hz, 1H), 4.40 (m, 1H), 3.72 (m, 1H), 3.63 (s, 3H), 3.45 (s, 3H), 2.76 (s, 3H), 1.99 (m, 2H), 1.76 (m, 2H), 1.58-1.65 (m, 4H), 1.33-1.43 (m, 4H), 1.15 (m, 1H) ppm. MS (ESI) m/z=534 [M+H]+.

Sources & evidence

ORD record
ord-5d573e3f92414fb1900ab94437b223c6
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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