1-(4-Aminophenyl)methanesulfonamide → [4-(4-{[2-(3-Fluoro-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride

HRID 1391574Notes

Reaction equation

HRID 1391574 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][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N: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:1].[F:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][NH:16][C:14]1[N:13]([CH3:25])[C:12]2[CH:26]=[CH:27][C:9]([N:8]([CH3:28])[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([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:7]=3)=[CH:10][C:11]=2[N:15]=1

Participants

3

Reactant 2

HCID 108214071-(4-Aminophenyl)methanesulfonamideHCID 59674229HCID 59674229, compound

Product 1

HCID 10218612[4-(4-{[2-(3-Fluoro-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 one with N5-(2-chloro-pyrimidin-4-yl)-N2-(3-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (99 mg, 0.25 mmol) and (4-amino-phenyl)-methanesulfonamide (46 mg, 0.25 mmol) as a white solid (111 mg, 76%). 1H NMR (300 MHz, dG-DMSO+NaHCO3) δ 10.03 (br s, 2H), 9.37 (br s, 1H), 7.87 (d, J=6.6 Hz, 1H), 7.54-7.64 (m, 2H), 7.32-7.44 (m, 3H), 7.19-7.24 (M, 3H), 7.08-7.14 (M, 1H), 6.81 (s, 2H), 5.82 (d, J=6.0 Hz, 1H), 4.76 (d, J=5.7 Hz, 2H), 4.18 (s, 2H), 3.72 (s, 3H), 3.47 (s, 3H). MS (ESI) m/z=547 [M+H].

Sources & evidence

ORD record
ord-48b833dab4ca483fbd6ccc6d0df580ce
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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