Potassium Carbonate → 5-[2-fluoro-4-(1H-tetrazol-1-yl)phenyl]-2-[1-(2-methoxyethyl)piperidin-4-yl]benzo[d]oxazole

HRID 710158

Reaction equation

HRID 710158 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:25][C:24]=2[CH:34]=1.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:46][CH2:47][O:48][CH3:49])(=O)=O.CCOC(C)=O.O>CN(C=O)C>[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:46][CH2:47][O:48][CH3:49])[CH2:32][CH2:33]3)=[N:25][C:24]=2[CH:34]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1462932-Methoxyethyl methanesulfonateHCID 22728543Water ethylacetateHCID 710900805-(2-fluoro-4-(1H-tetrazol-1-yl)phenyl)-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate

Product 1

HCID 711144675-[2-fluoro-4-(1H-tetrazol-1-yl)phenyl]-2-[1-(2-methoxyethyl)piperidin-4-yl]benzo[d]oxazoleYield 355.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[2-fluoro-4-(1H-tetrazol-1-yl)-phenyl]-2-(piperidin-4-yl)-benzo[d]oxazole 2,2,2-trifluoroacetate (30 mg, 0.06 mmol) was dissolved in DMF (2 ml) and added K2CO3 (40 mg, 0.29 mmol) and stirred the mixture at rt for 15 mins. To this mixture added 2-methoxyethyl methanesulfonate (45 mg, 0.29 mmol) and stirred at rt for 17 h. Work up (EtOAc/H2O) followed by purification by column chromatography on 60-120 mesh silicagel using a gradient mixture of DCM and MeOH (98:2) as eluent afforded the titled compound (90 mg) as a brown solid (15 mg). M.P.: 148-152° C. MS (m/z): 423.3 [M+H]+.

Workup

  1. stirringstirred at rt for 17 h
  2. customfollowed by purification by column chromatography on 60-120 mesh silicagel
  3. additiona gradient mixture of DCM and MeOH (98:2) as eluent

Sources & evidence

ORD record
ord-f1ee3165eaf94bba8b8407aa14598622
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Linked notes

Loading…