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

HRID 1391567Notes

Reaction equation

HRID 1391567 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:29])[C:9]2[CH:28]=[CH:27][C:12]3[N:13]([CH3:26])[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([CH3:41])=[C:35]([S:37]([NH2:40])(=[O:39])=[O:38])[CH:36]=1>>[ClH:1].[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]2[N:13]([CH3:26])[C:12]3[CH:27]=[CH:28][C:9]([N:8]([CH3:29])[C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C:31]5[CH:32]=[CH:33][C:34]([CH3:41])=[C:35]([S:37]([NH2:40])(=[O:38])=[O:39])[CH:36]=5)[N:7]=4)=[CH:10][C:11]=3[N:15]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 2355115-Amino-2-methylbenzenesulfonamideHCID 59674096HCID 59674096, compound

Product 1

HCID 692665595-(4-{[2-(4-Methoxy-benzylamino)-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 one with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-methoxy-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (82 mg, 0.20 mmol) and 5-amino-2-methyl-benzenesulfonamide (37 mg, 0.20 mmol) as a white solid (89 mg, 75%). 1H NMR (300 MHz, d6-DMSO+NaHCO3). δ 10.25 (br s, 2H), 9.50 (br s, 1H), 8.46 (s, 1H), 7.88 (d, J=6.6 Hz, 1H), 7.60-7.67 (m, 2H), 7.41-7.46 (m, 3H), 7.23-7.32 (m, 4H), 6.93 (d. J=8.7 Hz, 2H), 5.78 (d, J=6.3 Hz, 1H), 6.68 (d, J=5.7 Hz, 2H), 3.74 (s, 3H), 3.71 (s, 3H), 3.51 (s, 3H), 2.53 (s, 3H). MS (ESI) m/z=559 [M+H]+.

Sources & evidence

ORD record
ord-35fa68585e1d457fa3350dc4899f02b6
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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