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

HRID 1391582Notes

Reaction equation

HRID 1391582 reaction equation
[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH3:15])[C:12]2[CH:16]=[CH:17][C:18]([N:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[N:23]=3)[CH3:21])=[CH:19][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][S:37]([NH2:40])(=[O:39])=[O:38])=[CH:32][CH:31]=1>>[ClH:28].[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH3:15])[C:12]2[CH:16]=[CH:17][C:18]([N:20]([CH3:21])[C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([CH2:36][S:37]([NH2:40])(=[O:38])=[O:39])=[CH:32][CH:31]=4)[N:23]=3)=[CH:19][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 108214071-(4-Aminophenyl)methanesulfonamideHCID 59674155HCID 59674155, compound

Product 1

HCID 10196714(4-{4-[(2-Benzylamino-1-ethyl-1 H-benzoimidazol-5-yl)-methyl-amino]-pyrimidin-2-ylamino}-phenyl)-methanesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example two with N2-Benzyl-N5-(2-chloro-pyrimidin-4-yl)-1-ethyl-N5-methyl-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and (4-amino-phenyl)-methanesulfonamide (46 mg, 0.25 mmol) as a white solid (97 mg, 67%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.30 (s, 1H), 7.79 (d, J=6.0 Hz, 1H), 7.75 (d, J=8.7 Hz, 2H), 7.15-7.42 (M, 9H), 6.9+5 (d, J=8.1 Hz, 1H), 6.77 (s, 2H), 5.69 (d, J=6.0 Hz, 1H), 4.65 (d, J=5.7 Hz, 2H), 4.16-4.18 (m, 4H), 3.44 (s, 3H), 1.27 (t, J=7.2 Hz, 3H). MS (ESI) m/z=543 [M+H]+.

Sources & evidence

ORD record
ord-f943d18e6872416dbe6072c415731ed3
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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