Hydrochloric Acid → 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]vinyl}-1H-pyrazole-5-carboxylic acid

HRID 1630677ノート

反応式

HRID 1630677 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10](/[CH:17]=[CH:18]/[N:19]3[N:23]=[N:22][C:21]([C:24]([F:27])([F:26])[F:25])=[N:20]3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.ClC1C(N2C(C(OC)=O)=CC(/C=C/N3C(C(F)(F)F)=NN=N3)=N2)=NC=CC=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10](/[CH:17]=[CH:18]/[N:19]3[N:23]=[N:22][C:21]([C:24]([F:26])([F:25])[F:27])=[N:20]3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66587560methyl 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-1H-tetrazol-1-yl]vinyl}-1H-pyrazole-5-carboxylateHCID 66587669methyl 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]vinyl}-1H-pyrazole-5-carboxylate

生成物 1

HCID 666597181-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]vinyl}-1H-pyrazole-5-carboxylic acid収率 48.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

88.7 mg (0.23 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]vinyl}-1H-pyrazole-5-carboxylate and methyl 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-1H-tetrazol-1-yl]vinyl}-1H-pyrazole-5-carboxylate in a ratio of 66:34 were dissolved in 5.0 ml of ethanol, and 26.6 mg (0.29 mmol) of 45% strength aqueous sodium hydroxide solution were added. After 1 hour of stirring at room temperature, the mixture was diluted with water and acidified with dilute hydrochloric acid. The aqueous phase was extracted repeatedly with ethyl acetate and dried over magnesium sulphate. The solvent was distilled off under reduced pressure, which gave 43 mg (48% of theory) of 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]vinyl}-1H-pyrazole-5-carboxylic acid and 1-(3-chloropyridin-2-yl)-3-{(E)-2-[5-(trifluoromethyl)-1H-tetrazol-1-yl]vinyl}-1H-pyrazole-5-carboxylic acid in a ratio of 70:30. (logP: 2.79/2.86; MH+: 386.0/386.0; 1H-NMR (400 MHz, CD3CN, δ, ppm): 7.40 (m, 1H), 7.59 (m, 1H), 7.75 (m, 1H), 8.05 (m, 1H), 8.31 (m, 1H), 8.53 (m, 1H).)

後処理

  1. extractionThe aqueous phase was extracted repeatedly with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. distillationThe solvent was distilled off under reduced pressure, which

出典と根拠

ORDレコード
ord-b1988561d63d4a70a076fb13a50bd4da
出典データセット
uspto-grants-2014_07
特許番号
US08791139B2

反応ノート

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