Ammonium formate → HCID 68325614, 화합물

HRID 2403293노트

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HRID 2403293 반응식
C1(C(=[N:14][C:15]2[N:20]=[CH:19][C:18]([CH:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>CO>[NH2:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 2723923Ammonium formateHCID 86671395HCID 86671395, 화합물

생성물 1

HCID 68325614HCID 68325614, 화합물수율 73.4%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

To a stirred solution of tert-butyl (RS)-2-(6-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-carboxylate (370 mg) in methanol (20 ml) was added ammonium formate (789 mg). The reaction mixture was degassed by bubbling argon into the mixture for several minutes. 10% Palladium on activated charcoal (44 mg) was then added and the reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was then filtered through celite and the filtrate was concentrated in vacuo. The residue was taken up in EtOAc and the mixture was washed sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH) to afford tert-butyl (RS)-2-(6-aminopyridin-3-yl)morpholine-4-carboxylate (171 mg, 73%) as a light yellow oil. MS (ISP): 280.2 ([M+H]+).

후처리

  1. customThe reaction mixture was degassed
  2. customby bubbling argon into the mixture for several minutes
  3. addition10% Palladium on activated charcoal (44 mg) was then added
  4. filtrationThe reaction mixture was then filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. washthe mixture was washed sequentially with water and with saturated brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH)

출처 및 근거

ORD 기록
ord-694f8a67ddcd4c529a1b3c8b0895cfac
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802673B2

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