Cesium carbonate → 1-(2-(Cyanomethoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:43][C:44]#[N:45]>CN(C=O)C>[C:44]([CH2:43][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1)#[N:45]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a vial charged with 1-(2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (113 mg, 0.224 mmol) was added DMF (898 μl) and Cs2CO3 (219 mg, 0.673 mmol) and bromoacetonitrile (53.8 mg, 0.45 mmol) respectively. The mixture was heated to 60° C. overnight affording conversion to desired product fairly cleanly. m/z (ESI) 543.2 (M+H)+. The mixture was dried under reduced pressure and purified with a 25 g Interchim column (25 μm silica) ramping EtOAc in heptane (0-100%, 10% DCM throughout) affording product as a light brown solid. m/z (ESI) 543.2 (M+H)+
Sources & evidence
- ORD record
- ord-28265ecaf7ba4c9e87a85e47729a02b8
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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