Cyclopropylamine → HCID 86632368, 화합물

HRID 2428148노트

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HRID 2428148 반응식
[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH:21]=O)[CH:15]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([NH2:27])[CH2:26][CH2:25]1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][NH:27][CH:24]2[CH2:26][CH2:25]2)[CH:15]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 69828Cyclopropylamine2회HCID 4311764Sodium borohydrideHCID 86632367HCID 86632367, 화합물

생성물 1

HCID 86632368HCID 86632368, 화합물수율 73.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (4.30 g, 12.4 mmol) and cyclopropylamine (1.77 mL, 12.4 mmol) in MeOH (125 mL) was stirred for 2 h at rt. Cyclopropylamine (0.44 mL, 6.2 mmol) was added, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt. NaBH4 (935 mg, 24.7 mmol) was added in portions. The mixture was stirred for 1 h. The solvents were removed under reduced pressure, and the residue was taken in EtOAc (800 mL). The resulting mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 5:95) yielded the title compound (3.53 g, 73%). LC-MS: tR=0.83 min; ES+: 389.52.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureto cool to rt
  4. stirringThe mixture was stirred for 1 h
  5. customThe solvents were removed under reduced pressure
  6. washThe resulting mixture was washed with aq. sat. NaHCO3 and brine
  7. dry with materiallayer was dried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the crude by FC (MeOH/CH2Cl2 5:95)

출처 및 근거

ORD 기록
ord-cdf841c3b45f439999c4adbe942d0f31
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968720B2

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