1-Fluoro-4-(isocyanatomethyl)benzene → 1,1-Dicyclopropyl-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide

HRID 1713526

반응식

HRID 1713526 반응식
C1(COC([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:26])[O:18][C:19]([CH:23]4[CH2:25][CH2:24]4)([CH:20]4[CH2:22][CH2:21]4)[CH:13]3[CH2:12]2)=O)C=CC=CC=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([CH2:32][N:33]=[C:34]=[O:35])=[CH:30][CH:29]=1>C(O)C.[C].[Pd]>[CH:23]1([C:19]2([CH:20]3[CH2:22][CH2:21]3)[CH:13]3[CH2:12][N:11]([C:34]([NH:33][CH2:32][C:31]4[CH:30]=[CH:29][C:28]([F:27])=[CH:37][CH:36]=4)=[O:35])[CH2:16][CH2:15][N:14]3[C:17](=[O:26])[O:18]2)[CH2:25][CH2:24]1

참가 물질

5

반응물 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 68422186(Phenylmethyl)1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

생성물 1

HCID 231219031,1-Dicyclopropyl-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide수율 87%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

(Phenylmethyl)1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (0.18 g, 0.50 mmol) was dissolved in ethanol (10 mL). 10% Palladium carbon (17 mg) was added thereto, and the mixture was stirred under hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through Celite, the Celite was washed with ethanol, and the filtrate was concentrated under reduced pressure. The resulting 1,1-dicyclopropyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one was dissolved in tetrahydrofuran (10 mL). (4-Fluoro)benzyl isocyanate (0.25 mL, 2.0 mmol) was added thereto, and the mixture was stirred at 50° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:4) to obtain the title compound (0.16 g, 87% yield from (phenylmethyl) 1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate).

후처리

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe resulting 1,1-dicyclopropyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one was dissolved in tetrahydrofuran (10 mL)
  5. stirringthe mixture was stirred at 50° C. for 4 hours
  6. concentrationThe reaction solution was concentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:4)

출처 및 근거

ORD 기록
ord-4624d882f6804bfc8a6e39a5595b56cc
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795267B2

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