1-Butanol → (R)-ethyl 5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1631302노트

반응식

HRID 1631302 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[N:3]=1.Cl.Cl.[F:18][C:19]1[CH:20]=[C:21]([C@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[C:22]([O:25][CH3:26])=[N:23][CH:24]=1.C(N(C(C)C)CC)(C)C.C(O)CCC>CCOC(C)=O>[F:18][C:19]1[CH:20]=[C:21]([C@H:27]2[CH2:31][CH2:30][CH2:29][N:28]2[C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]3[N:3]=2)[C:22]([O:25][CH3:26])=[N:23][CH:24]=1

참가 물질

6

반응물 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 58063474Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylateHCID 66847679(R)-5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine dihydrochloride

생성물 1

HCID 86664565(R)-ethyl 5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate수율 56.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (Preparation B, 0.75 g, 3.32 mmol), (R)-5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine dihydrochloride (0.984 g, 3.66 mmol), diisopropylethylamine (2.32 mL, 13.3 mmol) and n-butanol (1.11 mL) were heated at 90° C. for 48 hours. The reaction mixture was diluted with EtOAc and the mixture was washed with water, brine and saturated NaHCO3. The organic layer was dried with MgSO4, filtered and concentrated afford a dark orange oil. The oil was purified by silica chromatography, eluting with a 50-80% EtOAc/Hexane gradient, to afford (R)-ethyl 5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.72 g, 56.2%) as a yellow foam. MS (apci) m/z=386.0 (M+H).

후처리

  1. washthe mixture was washed with water, brine and saturated NaHCO3
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customafford a dark orange oil
  6. customThe oil was purified by silica chromatography
  7. washeluting with a 50-80% EtOAc/Hexane gradient

출처 및 근거

ORD 기록
ord-17847951198f46e493b30f28472380b7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791123B2

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