Hydrochloric Acid → 5,7-Diphenyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

HRID 2260540

반응식

HRID 2260540 반응식
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20]([CH2:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[C:21]1([C:20]2[CH:28]=[C:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:6]3[N:5]=[C:4]([C:7]4[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=4)[C:3]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)=[C:2]3[N:1]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8433DibenzoylmethaneHCID 516892Sodium BicarbonateHCID 178509109HCID 178509109, 화합물

생성물 1

HCID 199572965,7-Diphenyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine수율 93.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (153 mg), dibenzoylmethane (162 mg) and conc. hydrochloric acid (0.1 ml) in ethanol (5 ml) was refluxed for 4 hours. The reaction mixture was cooled and poured into ice-water. The mixture was neutralized with an aqueous saturated sodium bicarbonate solution. The separated oil was extracted with dichloromethane and the extract was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from methanol to give 5,7-diphenyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (250 mg).

후처리

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThe separated oil was extracted with dichloromethane
  4. washthe extract was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. customthe obtained oil was crystallized from methanol

출처 및 근거

ORD 기록
ord-749ae22cdcd6485f9eb3aa43e11abbea
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05478827

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