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

HRID 1391587Notes

Reaction equation

HRID 1391587 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]=[CH:32][C:33]([CH3:40])=[C:34]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:35]=1>>[ClH:1].[CH3:40][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:2]2[N:7]=[C:6]([N:8]([CH3:28])[C:9]3[CH:27]=[CH:26][C:12]4[N:13]([CH3:25])[C:14]([NH:16][CH:17]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH3:18])=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:35][C:34]=1[S:36]([NH2:39])(=[O:38])=[O:37]

Participants

3

Reactant 2

HCID 2355115-Amino-2-methylbenzenesulfonamideHCID 59674124N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(1-phenyl-ethyl)-1H-benzoimidazole-2,5-diamine

Product 1

HCID 102185882-Methyl-5-(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 5-amino-2-methyl-benzenesulfonamide (46 mg, 0.25 mmol) as a white solid (90 mg, 63%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.85 (br s, 2H), 8.52 (s, 1H), 7.83 (d, J=6.3 Hz, 1H), 7.65-7.68 (dd, J=8.1 and 1.8 Hz, 1H), 7.51-7.57 (m, 3H), 7.34-7.39 (m, 2H), 7.25-7.30 (m, 4H), 7.15-7.22 (m, 2H), 5.70 (d, J=6.3 Hz, 1H), 5.22 (m, 1H), 3.74 (s, 3H), 3.47 (s, 3H), 2.51 (s, 3H), 1.63 (d, J=6.6 Hz, 3H). MS (ESI) m/z=543 [M+H]+.

Sources & evidence

ORD record
ord-01fdece5ddb049a1b8bc2927d760e564
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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