Ammonium Chloride → 3-{8-(3,4-Difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-3-ol

HRID 71170

反応式

HRID 71170 の反応式
[CH2:1]([Mg]Br)[CH3:2].[F:5][C:6]1[CH:7]=[C:8]([CH:38]=[CH:39][C:40]=1[F:41])[O:9][C:10]1([C:33](OCC)=[O:34])[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28]([CH3:30])=[N:27][CH:26]=4)=[C:21]([O:31][CH3:32])[CH:20]=3)=[N:17][N:18]=[C:11]12.[Cl-].[NH4+]>C1COCC1>[F:5][C:6]1[CH:7]=[C:8]([CH:38]=[CH:39][C:40]=1[F:41])[O:9][C:10]1([CH:33]([OH:34])[CH2:1][CH3:2])[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28]([CH3:30])=[N:27][CH:26]=4)=[C:21]([O:31][CH3:32])[CH:20]=3)=[N:17][N:18]=[C:11]12

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 66609151Ethyl 8-(3,4-difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateHCID 178418443HCID 178418443、化合物

生成物 1

HCID 666038153-{8-(3,4-Difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-3-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere, ethylmagnesium bromide (1 M THF solution, 11.8 mL) was added to a suspension of ethyl 8-(3,4-difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1200 mg) in THF (12 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hr, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (400 mg).

後処理

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-f111b50a36664cc7b4c442e94bea9b95
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

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