Ammonia → 2-(5-fluoro-2-(6-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25](=[O:42])(=[O:41])[N:26]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[C:27]4[S:28][CH:29]=[CH:30][N:31]=4)=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11]CC)=O.[NH3:43]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25](=[O:42])(=[O:41])[N:26]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[C:27]4[S:28][CH:29]=[CH:30][N:31]=4)=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([NH2:43])=[O:11]Participants
Conditions
- Temperature
- 60 °C
Procedure
Ethyl 2-(5-fluoro-2-(6-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetate was dissolved in methanolic ammonia and heated at 60° C. for 16 h in a sealed tube. The reaction mixture was concentrated to obtain 2-(5-fluoro-2-(6-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetamide as light yellow solid. m/z (ESI) 579.2 (M+H)+. This was then dissolved in DCM (1 mL) and 4 drops of TFA were added and the reaction was stirred for 15 min. The reaction mixture was loaded on 10 g silica gel column and eluted with DCM:MeOH (90:10) up to 100% to obtain 2-(5-fluoro-2-(6-(N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetamide (3.9 mg, 8.51 μmol, 2.96% yield) as light yellow solid. m/z (ESI) 459.0 (M+H)+.
Workup
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-80c689795c4e4d9e8b6b046a214b2050
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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