5-Amino-2-methylbenzenesulfonamide → (1-Methyl-5-{methyl-[2-(4-methyl-3-sulfamoyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-phenyl-carbamic acid tert-butyl ester hydrochloride
Reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([N:24]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([Cl:32])[N:27]=3)[CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH3:45])=[C:39]([S:41]([NH2:44])(=[O:43])=[O:42])[CH:40]=1>>[ClH:32].[C:1]([O:5][C:6](=[O:33])[N:7]([C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([N:24]([CH3:25])[C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:34][C:35]4[CH:36]=[CH:37][C:38]([CH3:45])=[C:39]([S:41](=[O:43])(=[O:42])[NH2:44])[CH:40]=4)[N:27]=3)=[CH:23][C:16]=2[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
The title compound was prepared following the procedure of example 60 using {5-[(2-Chloro-pyrimidin-4-yl)-methyl-amino]-1-methyl-1H-benzoimidazol-2-yl}-phenyl-carbamic acid tert-butyl ester (100 mg, 0.22 mmol) and 5-amino-2-methyl-benzenesulfonamide (41 mg, 0.22 mmol) to give the desired product as a white solid. 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.48 (s, 1H), 8.54 (s, 1H), 7.79 (d, J=6.3 Hz, 1H), 7.66-7.71 (M, 2H), 7.56 (d, J=1.5 Hz, 1H), 7.38 (m, 4H), 7.23-7.29 (m, 4H), 7.12 (m, 1H), 5.68 (d, J=6.0 Hz, 1H), 3.78 (s, 3H), 3.48 (s, 3H), 2.49 (s, 3H), 1.42 (s, 9H). MS (ESI) m/z=615 [M+H]+.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-9572a66cb2664ca4a50f64f121a19f83
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338959B2
Reaction notes
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