Dimethylformamide → tert-Butyl{3-[4-(2-fluoroethoxy)-2,6-dimethoxyphenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate

HRID 41278

Reaction equation

HRID 41278 reaction equation
CN(C=O)C.[C:6]([O:10][C:11](=[O:34])[NH:12][C:13]1[C:14]([O:32][CH3:33])=[N:15][N:16]2[C:20]([C:21]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([OH:29])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:19][S:18][C:17]=12)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].I[CH2:42][CH2:43][F:44]>O>[C:6]([O:10][C:11](=[O:34])[NH:12][C:13]1[C:14]([O:32][CH3:33])=[N:15][N:16]2[C:20]([C:21]3[C:22]([O:30][CH3:31])=[CH:23][C:24]([O:29][CH2:42][CH2:43][F:44])=[CH:25][C:26]=3[O:27][CH3:28])=[CH:19][S:18][C:17]=12)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 44479005Tert-butyl[3-(4-hydroxy-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

Product 1

HCID 58223410tert-Butyl{3-[4-(2-fluoroethoxy)-2,6-dimethoxyphenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (2.28 ml) solution of tert-butyl[3-(4-hydroxy-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate (115 mg, 0.273 mmol) were added potassium carbonate (49.0 mg, 0.355 mmol) and 1-iodo-2-fluoroethane (61.7 mg, 0.355 mmol), and the mixture was stirred at room temperature for 20 hours and 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product of the title compound (128 mg, 0.273 mmol)

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ccaf200e165e40398a255094fdf05669
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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