Ammonium Acetate → (rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

HRID 714097노트

반응식

HRID 714097 반응식
C([O-])(=O)C.[NH4+].[F:6][C:7]1[CH:8]=[C:9]([C:17]2[C:25]3[CH2:24][CH2:23][C:22](=O)[C:21]=3[CH:20]=[N:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].C([BH3-])#[N:28].[Na+]>CO.C(O)C>[F:6][C:7]1[CH:8]=[C:9]([C:17]2[C:25]3[CH2:24][CH2:23][CH:22]([NH2:28])[C:21]=3[CH:20]=[N:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14]

참가 물질

6

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 898462884-(3-Fluoro-4-trifluoromethyl-phenyl)-5,6-dihydro-[2]pyrindin-7-one

생성물 1

HCID 71811529(rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

A solution of ammonium acetate (117 mg, 1.52 mmol) in MeOH (1 mL) was treated with 4-(3-fluoro-4-trifluoromethyl-phenyl)-5,6-dihydro-[2]pyrindin-7-one (intermediate A-14 [C1]) (15 mg, 0.051 mmol) dissolved in ethanol (0.5 mL) and the reaction mixture stirred at room temperature for 1 h. Sodium cyanoborohydride (11.2 mg, 0.18 mmol) was added and stirring continued at room temperature. After 15 min, the reaction mixture was heated to reflux for 30 min. The solvent was removed under reduced pressure, a sat. aq. solution of ammonium chloride (2 mL) and a 1 M solution of HCl (1 mL) were added and the aq. phase washed with dichloromethane (3×5 mL). To the aq. phase was added a 1 M solution of NaOH (2 mL) and extracted with dichloromethane (3×5 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The title compound was isolated as light brown solid (3.8 mg, 25%). MS: 297.4 (M+H)+.

후처리

  1. stirringstirring
  2. customcontinued at room temperature
  3. waitAfter 15 min
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for 30 min
  6. customThe solvent was removed under reduced pressure
  7. additiona sat. aq. solution of ammonium chloride (2 mL) and a 1 M solution of HCl (1 mL) were added
  8. washthe aq. phase washed with dichloromethane (3×5 mL)
  9. additionTo the aq. phase was added a 1 M solution of NaOH (2 mL)
  10. extractionextracted with dichloromethane (3×5 mL)
  11. dry with materialThe combined organic phases were dried over MgSO4
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e2f0cb63cdb1498a812a1e9c40abf214
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187429B2

반응 노트

불러오는 중…