Methyl chloroacetate → 7-tert-Butyl 1-methyl 3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylate

HRID 1895638노트

반응식

HRID 1895638 반응식
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]2[C:20]([C:24]([F:27])([F:26])[F:25])=[N:21][C:22](Br)=[C:16]2[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].ClC[C:30]([O:32][CH3:33])=[O:31]>CO.[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[CH3:33][O:32][C:30]([C:22]1[N:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:17]2[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][C:16]=12)=[O:31]

참가 물질

6

반응물 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 57518451tert-butyl 1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo(1,5-a)pyrazine-7-carboxylate

생성물 1

HCID 575184527-tert-Butyl 1-methyl 3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylate수율 67.8%

시약·촉매·용매 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)촉매HCID 887Methanol용매

실험 절차

Octacarbonyldicobalt (5.54 g, 16.2 mmol) and potassium carbonate (11.2 g, 81.1 mmol) was dissolved in 100 mL of methanol under stirring. The reaction mixture was stirred for 15 minutes at 60° C., and 1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 27b (3 g, 8.11 mmol) and methyl chloroacetate (5.25 g, 48.6 mmol) were then added to the solution. The reaction mixture was reacted for 6 hours under a carbon monoxide atmosphere and monitored by thin layer chromatography until the disappearance of the starting materials. After cooling to room temperature, the reaction mixture was filtered through a pad of silica gel, rinsed with methanol. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester 1-methyl ester 27c (1.92 g, yield 67%) as a white solid. (Reference: J. Organomet. Chem., 1985, 293)

후처리

  1. stirringThe reaction mixture was stirred for 15 minutes at 60° C.
  2. customThe reaction mixture was reacted for 6 hours under a carbon monoxide atmosphere
  3. filtrationthe reaction mixture was filtered through a pad of silica gel
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-48b8391e67f5428b86e6b99f05cbdd99
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513411B2

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