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

HRID 1391627Notes

Reaction equation

HRID 1391627 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:21])[C:9]2[CH:20]=[CH:19][C:12]3[N:13]([CH3:18])[C:14]([NH:16][CH3:17])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1>>[CH3:21][N:8]([C:9]1[CH:20]=[CH:19][C:12]2[N:13]([CH3:18])[C:14]([NH:16][CH3:17])=[N:15][C:11]=2[CH:10]=1)[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:22][C:23]2[CH:24]=[C:25]([S:29]([NH2:32])(=[O:30])=[O:31])[CH:26]=[CH:27][CH:28]=2)[N:7]=1

Participants

3

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 59674195N5-(2-chloropyrimidin-4-yl)-N2,N5,1-trimethyl-1H-benzimidazole-2,5-diamine

Product 1

HCID 596742183-{4-[Methyl-(1-methyl-2-methylamino-1H-benzoimidazol-5-yl)-amino]-pyrimidin-2-ylamino}-benzenesulfonamide

Procedure

The title compound was prepared following the procedure of Example 1 with N5-(2-chloropyrimidin-4-yl)-N2,N5,1-trimethyl-1H-benzimidazole-2,5-diamine (60 mg, 0.20 mmol) and 3-amino-benzenesulfonamide (34 mg, 0.20 mmol) as a white solid (40 mg, 42%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.51 (s, 1H), 8.61 (s, 1H), 7.77-7.82 (M, 2H), 7.26-7.39 (m, 6H), 7.17 (s, 1H), 6.92 (d, J=7.8 Hz, 1H), 5.66 (d, J=6.0 Hz, 1H), 3.55 (s, 3H), 3.47 (s, 3H), 2.95 (d, J=4.2 Hz, 3H). MS (ESI) m/z=439 [M+H]+.

Sources & evidence

ORD record
ord-cacf830945f5424f82f62c88f60804b6
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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