Hydrochloric Acid → 7-Cyclohexyl-6-[4-(3-methoxyphenyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 460691노트

반응식

HRID 460691 반응식
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)=[CH:23][CH:22]=3)[CH:12]=[N:11][C:10]=12)=[O:5])C.[Li+].[OH-].Cl>O1CCCC1>[CH:15]1([C:14]2[N:9]3[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]3[N:11]=[CH:12][C:13]=2[C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)=[CH:25][CH:26]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 691552937-Cyclohexyl-6-(3'-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester

생성물 1

HCID 159581197-Cyclohexyl-6-[4-(3-methoxyphenyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid수율 34.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 47 mg (0.103 mmol) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester in 3 mL of tetrahydrofuran was added 0.62 mL (0.62 mmol) of 1 M LiOH solution, and the resulting mixture was heated at reflux overnight. The reaction mixture was then acidified with 1 M HCl solution to pH=2, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 15 mg (34% yield) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (446) as a solid (90% purity) as indicated by 1H NMR; LC-MS—calcd for C26H25N3O3 [M++H]+: 428.19, found: 428.2.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified via reverse-phase chromatography

출처 및 근거

ORD 기록
ord-619ed55f65e84eaab43412e7f8e5501e
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196111B2

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