tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (R)-tert-Butyl 3-(2-chloro-5-fluoro-6-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 573995노트

반응식

HRID 573995 반응식
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Cl:15][C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:19]([F:28])=[C:18](Cl)[N:17]=1>C(O)C>[Cl:15][C:16]1[N:17]=[C:18]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[C:19]([F:28])=[C:20]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:21]=1

참가 물질

4

반응물 2

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 866441264-(2,6-Dichloro-5-fluoropyrimidin-4-yl)morpholine

생성물 1

HCID 90409880(R)-tert-Butyl 3-(2-chloro-5-fluoro-6-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate수율 48.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(R)-tert-Butyl 3-aminopiperidine-1-carboxylate (1.60 g, 7.99 mmol) was added to a solution of 4-(2,6-dichloro-5-fluoropyrimidin-4-yl)morpholine (Preparation 11a, 1.01 g, 4.00 mmol) in ethanol (48 mL) and the resulting mixture was stirred and heated to reflux for 3 days. After cooling to ambient temperature, the solvent was evaporated under reduced pressure and the residue was partitioned between water and methylene chloride. The organic layer was separated, washed with water, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (0-100% ethyl acetate in hexanes) to give the title compound (0.810 g, 47%) as a white foam.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 days
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between water and methylene chloride
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated under reduced pressure
  9. customThe residue was purified by flash chromatography (0-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-481a68890fe54af89ae200b3fe852551
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034311B2

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