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

HRID 1391623Notes

Reaction equation

HRID 1391623 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:26])[C:9]2[CH:25]=[CH:24][C:12]3[N:13]([CH3:23])[C:14]([NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH3:38])=[C:32]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:33]=1>>[ClH:1].[CH:17]1([NH:16][C:14]2[N:13]([CH3:23])[C:12]3[CH:24]=[CH:25][C:9]([N:8]([CH3:26])[C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:27][C:28]5[CH:29]=[CH:30][C:31]([CH3:38])=[C:32]([S:34]([NH2:37])(=[O:35])=[O:36])[CH:33]=5)[N:7]=4)=[CH:10][C:11]=3[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 2355115-Amino-2-methylbenzenesulfonamideHCID 59674146HCID 59674146, compound

Product 1

HCID 692663645-{4-[(2-Cyclohexylamino-1-methyl-1H-benzoimidazol-5-yl)-methyl-amino]-pyrimidin-2-ylamino}-2-methyl-benzenesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example 1 with N5-(2-Chloro-pyrimidin-4-yl)-N2-cyclohexyl-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (92 mg, 0.25 mmol) and 5-amino-2-methyl-benzenesulfonamide (46 mg, 0.25 mmol) as a white solid (95 mg, 68%). 1H NMR (300 MHz, D6-DMSO) δ 9.51 (s, 1H), 8.56 (s, 1H), 8.18 (br s, 1H), 7.83 (d, J=6.0 Hz, 1H), 7.69 (dd, J=8.4 and 2.1 Hz, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.30 (s, 1H), 7.24 (s, 2H), 7.13-7.18 (M, 2H), 5.69 (d, J=6.0 Hz, 1H), 3.70 (m, 1H), 3.64 (s, 3H), 3.47 (s, 3H), 2.50 (s, 3H), 1.98-2.01 (m, 2H), 1.76-1.79 (m, 2H), 1.62—1.66 (m, 1H), 1.29-1.48 (m, 4H), 1.14-1.17 (m, 1H) ppm. MS (ESI) m/z=521 [M+H]+.

Sources & evidence

ORD record
ord-97a8ddbe70744859b4c898350e3681ef
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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