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

HRID 1391626Notes

Reaction equation

HRID 1391626 reaction equation
[Cl:1][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]=[CH:25][C:26]([CH3:33])=[C:27]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:28]=1>>[ClH:1].[CH3:33][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:2]2[N:7]=[C:6]([N:8]([CH3:21])[C:9]3[CH:20]=[CH:19][C:12]4[N:13]([CH3:18])[C:14]([NH:16][CH3:17])=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:28][C:27]=1[S:29]([NH2:32])(=[O:31])=[O:30]

Participants

3

Reactant 2

HCID 2355115-Amino-2-methylbenzenesulfonamideHCID 59674195N5-(2-chloropyrimidin-4-yl)-N2,N5,1-trimethyl-1H-benzimidazole-2,5-diamine

Product 1

HCID 692655612-Methyl-5-{4-[methyl-(1-methyl-2-methylamino-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-chloropyrimidin-4-yl)-N2,N5,1-trimethyl-1H-benzimidazole-2,5-diamine (58 mg, 0.20 mmol) and 5-amino-2-methyl-benzenesulfonamide (35 mg, 0.20 mmol) as a pink solid (78 mg, 84%). 1H NMR (300 MHz, d6-DMSO) δ 10.63 (br s, 1H), 9.22 (d, J=4.2 Hz, 1H), 8.40 (br s, 2H), 7.91 (d, J=6.9 Hz, 1H), 7.67 (m, 2H), 7.47 (d, J=1.5 Hz, 1H), 7.28-7.36 (m, 3H), 5.83 (m, 1H), 3.67 (s, 3H), 3.53 (s, 3H), 3.08 (d, J=4.5 Hz, 3H), 2.54 (s, 3H). MS (ESI) m/z=453 [M+H]+.

Sources & evidence

ORD record
ord-4684148309de4a36a2d78161eb693d4d
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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