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

HRID 1473588Notes

Reaction equation

HRID 1473588 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([OH:36])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:44][C:45]#[N:46]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:19])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([O:36][CH2:44][C:45]#[N:46])[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 1364090691-(4-Chloro-2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Product 1

HCID 866876501-(4-Chloro-2-(cyanomethoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To the crude material from Step 1 was added DMF (1.5 ml) followed by cesium carbonate (175 mg, 0.538 mmol) and bromoacetonitrile (24.99 μl, 0.359 mmol). The resulting mixture was stirred at 60° C. overnight affording clean conversion to desired product according to LC-MS. The mixture was filtered through Celite with the aid of DCM and the filtrate dried under reduced pressure. m/z (ESI) 577.1 (M+H)+.

Sources & evidence

ORD record
ord-20b3972d8a9949498d2369236e81365e
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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