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

HRID 1391562Notes

Reaction equation

HRID 1391562 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][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=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].[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]2[N:13]([CH3:25])[C:12]3[CH:26]=[CH:27][C:9]([N:8]([CH3:28])[C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:29][C:30]5[CH:31]=[CH:32][C:33]([CH3:40])=[C:34]([S:36]([NH2:39])(=[O:37])=[O:38])[CH:35]=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 59674181N5-(2-chloro-pyrimidin-4-yl)-N2-(4-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine

Product 1

HCID 102399785-(4-{[2-(4-Fluoro-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-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (99 mg, 0.25 mmol) and 5-amino-2-methyl-benzenesulfonamide (47 mg, 0.25 mmol) as a white solid (69 mg, 48%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ10.28 (br s, 1H), 9.61 (br s, 1H), 8.45 (s, 1H), 7.86 (d, J=2.1 Hz, 1H), 7.63 (m, 1H), 7.52-7.59 (m, 3H), 7.37 (s, 1H), 7.31 (s, 2H), 7.13-7.26 (m, 4H), 5.74 (d, J=4.5 Hz, 1H), 4.73 (d, J=4.5 Hz, 2H), 3.71 (s, 3H), 3.48 (s, 3H), 2.50 (s, 3H). MS (ESI) m/z=547 [M+H]+.

Sources & evidence

ORD record
ord-054da39c55c242debaabc1e124f5ee82
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

Loading…