Hydrochloric Acid → 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-((S)-2,3-dihydroxypropoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1631367노트

반응식

HRID 1631367 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([NH:25][O:26][CH2:27][C@@H:28]3[CH2:32][O:31]C(C)(C)[O:29]3)=[O:24])=[C:16]2[N:15]=1.Cl>C1COCC1.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([NH:25][O:26][CH2:27][C@@H:28]([OH:29])[CH2:32][OH:31])=[O:24])=[C:16]2[N:15]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 866645775-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide

생성물 1

HCID 867625725-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-((S)-2,3-dihydroxypropoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide (135 mg, 0.285 mmol) in THF (4.0 mL) was added 6M HCl (1.0 mL) dropwise and the mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was concentrated to approximately 1 mL and was diluted with H2O (5 mL). The resulting milky white mixture was extracted with EtOAc and the combined extracts were washed with 1M Na2CO3 and saturated NaCl. The EtOAc solution was dried over MgSO4 and filtered through a packed Celite pad capped with a layer of MgSO4. The solution was concentrated to give a colorless foam that was dissolved in minimal CH2Cl2 and treated with hexanes to give a white suspension. The suspension was concentrated to give the title compound as a white solid that was dried in vacuum (102 mg, 82%). MS (apci) m/z=434.0 (M+H).

후처리

  1. concentrationThe reaction mixture was concentrated to approximately 1 mL
  2. additionwas diluted with H2O (5 mL)
  3. extractionThe resulting milky white mixture was extracted with EtOAc
  4. washthe combined extracts were washed with 1M Na2CO3 and saturated NaCl
  5. dry with materialThe EtOAc solution was dried over MgSO4
  6. filtrationfiltered through a packed Celite pad
  7. customcapped with a layer of MgSO4
  8. concentrationThe solution was concentrated
  9. customto give a colorless foam that
  10. customto give a white suspension
  11. concentrationThe suspension was concentrated

출처 및 근거

ORD 기록
ord-bf2a84e1c6eb4adca48b2e6e17073c63
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791123B2

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