1-(4-Aminophenyl)methanesulfonamide → [4-(4-{[2-(4-Methoxy-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride

HRID 1391569Notes

Reaction equation

HRID 1391569 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.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][S:38]([NH2:41])(=[O:40])=[O:39])=[CH:33][CH:32]=1>>[ClH:1].[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]2[N:13]([CH3:26])[C:12]3[CH:27]=[CH:28][C:9]([N:8]([CH3:29])[C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([CH2:37][S:38]([NH2:41])(=[O:39])=[O:40])=[CH:33][CH:32]=5)[N:7]=4)=[CH:10][C:11]=3[N:15]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 108214071-(4-Aminophenyl)methanesulfonamideHCID 59674096HCID 59674096, compound

Product 1

HCID 10196823[4-(4-{[2-(4-Methoxy-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-phenyl]-methanesulfonamide 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-amino-phenyl)-methanesulfonamide (37 mg, 0.20 mmol) as a white solid (49 mg, 41%). 1H NMR (300 MHz, d6-DMSO) δ 9.58 (br s, 1H), 9.00 (br s, 1H), 7.85 (d, J=6.0 Hz, 1H), 7.68 (d, J=8.1 Hz, 2H), 7.42-7.50 (M, 3H), 7.29 (s, 1H), 7.12-7.21 (m, 3H), 6.91 (d, J=8.4 Hz, 2H), 6.80 (s, 2H), 5.75 (d, J=5.7 Hz, 1H), 4.64 (d, J=5.1 Hz, 2H), 4.17 (s, 2H), 3.73 (s, 3H), 3.68 (s, 3H), 3.46 (s, 3H). MS (ESI) m/z=559 [M+H]+.

Sources & evidence

ORD record
ord-cd53976626d34c55abccde81fa65ef47
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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