Cesium carbonate → HCID 86687671, compound

HRID 1473607Notes

Reaction equation

HRID 1473607 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][N:6]([C:28]1[S:29][CH:30]=[CH:31][N:32]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26])=[N:15][CH:14]=[C:13]2[F:27])(=[O:9])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:46][C:47]#[N:48]>CN(C=O)C.C(OCC)(=O)C>[C:47]([CH2:46][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:16]1[C:17]2[C:12](=[CH:11][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:3]=3[O:2][CH3:1])[C:28]3[S:29][CH:30]=[CH:31][N:32]=3)(=[O:8])=[O:9])=[CH:19][CH:18]=2)[C:13]([F:27])=[CH:14][N:15]=1)#[N:48]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 136409072HCID 136409072, compound

Product 1

HCID 86687671HCID 86687671, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-(2,4-dimethoxybenzyl)-4-fluoro-1-(2-hydroxyphenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (0.078 g, 0.141 mmol) was dissolved in DMF (0.7 mL) and cesium carbonate (0.148 g, 0.456 mmol) was added, followed by bromoacetonitrile (10.58 μl, 0.152 mmol). The reaction was heated to 60° C. and stirred overnight. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-100% EtOAc:Heptane) to afford 1-(2-(cyanomethoxy)phenyl)-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(thiazol-2-yl)isoquinoline-6-sulfonamide. (ESI) 591.2 (M+H)+.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-f7f3de59dacc4965b39a6767963a3bea
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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