Benzenesulfonamide, 3-amino- → 3-(4-{Methyl-[1-methyl-2-(1-phenyl-ethylamino)-1H-benzoimidazol-5-yl]-amino}-pyrimidin-2-ylamino)-benzenesulfonamide hydrochloride

HRID 1391586Notes

Reaction equation

HRID 1391586 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][CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH3:18])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:29][C:30]1[CH:31]=[C:32]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1>>[ClH:1].[CH3:28][N:8]([C:9]1[CH:27]=[CH:26][C:12]2[N:13]([CH3:25])[C:14]([NH:16][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[N:15][C:11]=2[CH:10]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:29][C:30]2[CH:31]=[C:32]([S:36]([NH2:39])(=[O:37])=[O:38])[CH:33]=[CH:34][CH:35]=2)[N:7]=1

Participants

3

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 59674124N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine

Product 1

HCID 101751063-(4-{Methyl-[1-methyl-2-(1-phenyl-ethylamino)-1H-benzoimidazol-5-yl]-amino}-pyrimidin-2-ylamino)-benzenesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example one with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 3-amino-benzenesulfonamide (43 mg, 0.25 mmol) as a white solid (65 mg, 46%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.58 (s, 2H), 8.57 (s, 1H), 7.75-7.81 (m, 2H), 7.48-7.51 (m, 2H), 7.32-7.41 (m, 5H), 7.17-7.26 (m, 4H), 6.98-7.00 (m, 1H), 5.65 (d, J=6.3 Hz, 1H), 5.17 (m, 1H), 3.67 (s, 3H), 3.44 (s, 3H), 1.58 (d, J=6.9 Hz, 3H). MS (ESI) m/z=529 [M+H]+.

Sources & evidence

ORD record
ord-e4e3f1a74cff4857a5edcf349deed68a
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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