Cesium carbonate → 1-(2-(Cyanomethoxy)-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

HRID 1473591Notes

Reaction equation

HRID 1473591 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:47][C:48]#[N:49]>CN(C=O)C>[C:48]([CH2:47][O:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1)#[N:49]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 1364090701-(2-Hydroxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Product 1

HCID 866876541-(2-(Cyanomethoxy)-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a vial charged with 1-(2-hydroxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (111 mg, 0.194 mmol) was added DMF (777 μl) and Cs2CO3 (190 mg, 0.583 mmol) and bromoacetonitrile (46.6 mg, 0.39 mmol) respectively. The mixture was heated to 60° C. overnight affording conversion to desired product fairly cleanly. The mixture was dried under reduced pressure and purified with a 25 g Interchim column (25 um silica) ramping EtOAc in heptane (0-100%, 10% DCM throughout) affording product as a light brown solid. m/z (ESI) 611.3 (M+H)+

Sources & evidence

ORD record
ord-b9922989cf424ecebd9f3c2c4cee1e57
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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