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

HRID 710158

反応式

HRID 710158 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-f1ee3165eaf94bba8b8407aa14598622
出典データセット
uspto-grants-2015_11
特許番号
US09181214B2

関連ノート

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