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

HRID 1391618Notes

Reaction equation

HRID 1391618 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][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[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][CH2:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[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 59674177N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-phenethyl-1H-benzoimidazole-2,5-diamine

Product 1

HCID 101290632-Methyl-5-{4-[methyl-(1-methyl-2-phenethylamino-1H-benzoimidazol-5-yl)-amino]-pyrimidin-2-ylamino}-benzenesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example 1 with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-phenethyl-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 (88 mg, 61%). 1H NMR (400 MHz, d6-DMSO) δ 10.25 (br s, 1H), 9.22 (br s, 1H), 8.44 (s, 1H), 7.87 (d, J=6.8 Hz, 1H), 7.58-7.64 (m, 2H), 7.18-7.41 (m, 10H), 5.75 (d, J=5.6 Hz, 1H), 3.68-3.73 (m, 2H), 3.66 (s, 3H), 3.48 (s, 3H), 2.97 (m, 2H), 2.50 (s, 3H) ppm. MS (ESI) m/z=543 [M+H]+.

Sources & evidence

ORD record
ord-daf0e83213a242bcb21ee18ff2de6861
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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