Benzenesulfonamide, 3-amino- → 3-[4-(1-Methyl-2-phenethylamino-1H-benzoimidazol-5-ylamino)-pyrimidin-2-ylamino]-benzenesulfonamide hydrochloride

HRID 1391617Notes

Reaction equation

HRID 1391617 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8](C)[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]=[C:32]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1>>[ClH:1].[CH3:25][N:13]1[C:12]2[CH:26]=[CH:27][C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:29][C:30]4[CH:31]=[C:32]([S:36]([NH2:39])(=[O:37])=[O:38])[CH:33]=[CH:34][CH:35]=4)[N:7]=3)=[CH:10][C:11]=2[N:15]=[C:14]1[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 59674177N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-phenethyl-1H-benzoimidazole-2,5-diamine

Product 1

HCID 692652033-[4-(1-Methyl-2-phenethylamino-1H-benzoimidazol-5-ylamino)-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 3-amino-benzenesulfonamide (43 mg, 0.25 mmol) as a white solid (95 mg, 67%). 1H NMR (400 MHz, d6-DMSO) δ 9.83 (br s, 1H), 9.04 (br s, 1H), 8.49 (s, 1H), 7.87 (d, J=6.0 Hz, 1H), 7.72-7.74 (m, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.18-7.40 (m, 11H), 5.72 (d, J=5.6 Hz, 1H), 3.65-3.71 (m, 2H), 3.64 (s, 3H), 3.46 (s, 3H), 2.96 (m, 2H) ppm. MS (ESI) m/z=529 [M+H]+.

Sources & evidence

ORD record
ord-00fc590724df44c68973a95a8ef70a57
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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