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

HRID 710158

반응식

HRID 710158 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f1ee3165eaf94bba8b8407aa14598622
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181214B2

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