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

HRID 1630677노트

반응식

HRID 1630677 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).)

후처리

  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

출처 및 근거

ORD 기록
ord-b1988561d63d4a70a076fb13a50bd4da
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791139B2

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