N-(3-Aminophenyl)methanesulfamide → N-(3-((5-(isoquinolin-6-yl)oxazol-2-yl)amino)phenyl)methane sulfonamide

HRID 1035834Notes

Reaction equation

Cl[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[N:12][CH:11]=[CH:10]3)=[CH:5][N:6]=1.[NH2:17][C:18]1[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=1>CC(O)C>[CH:13]1[C:14]2[C:9](=[CH:8][C:7]([C:4]3[O:3][C:2]([NH:17][C:18]4[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=4)=[N:6][CH:5]=3)=[CH:16][CH:15]=2)[CH:10]=[CH:11][N:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-5-(isoquinolin-6-yl)oxazole 14 (0.15 g, 0.652 mmol) and commercially available N-(3-aminophenyl)methanesulfonamide 6 (0.121 g, 0.649 mmol) in 2-propanol (20 mL) was heated to 80° C. for 12 h with stirring. Additional one more equivalent of N-(3-aminophenyl)methanesulfonamide 6 (0.121 g, 0.649 mmol) was added to reaction mixture and heated to 80° C. for further 12 h with stirring. Upon cooling, solvent was evaporated and silica column purified (Biotage) (Acetone/hexane as an eluent) to provide N-(3-((5-(isoquinolin-6-yl)oxazol-2-yl)amino)phenyl)methane sulfonamide 59 (0.09 g, 38% yield) as pale yellow solid. MS (ES) m/z 381 (M+H+).

Workup

temperatureheated to 80° C. for further 12 h
stirringwith stirring
temperatureUpon cooling
customsolvent was evaporated
customsilica column purified (Biotage) (Acetone/hexane as an eluent)

Sources & evidence

ORD record: ord-8ed1a090ef4546a78b63c027f895afeb
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546400B2

Reaction notes

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