Benzenesulfonamide, 3-amino- → (1-Methyl-5-(methyl-[2-(3-sulfamoyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-phenyl-carbamic acid tert-butyl ester hydrochloride

HRID 1391604Notes

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]=[C:37]([S:41]([NH2:44])(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1>C(O)C.Cl>[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:40]=[CH:39][CH:38]=[C:37]([S:41](=[O:43])(=[O:42])[NH2:44])[CH:36]=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

Conditions

Temperature: 70 °C

Procedure

To a solution of {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 3-amino-benzenesulfonamide (38 mg, 0.22 mmol) in ethanol was added HCl (1 drop, 1M in diethyl ether), and the reaction was heated to 70° C. After 20 h, the reaction was filtered to give the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 10.15 (s, 1H), 8.44 (s, 1H), 7.84 (d, J=6.6 Hz, 1H), 7.72 (d, J=8.4 Hz, 2H), 7.61 (s, 1H), 7.27-7.39 (m, 10H), 5.79 (d, J=5.1 Hz, 1H), 3.78 (s, 3H), 3.51 (s, 3H), 1.41 (s, 9H). MS (ESI) m/z=601 [M+H]+.

Workup

filtrationthe reaction was filtered

Sources & evidence

ORD record: ord-50b30376f7e94d3bbca5e1525ff7dec0
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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