Piperidine → HCID 68649686, 화합물

HRID 1042382노트

반응식

HRID 1042382 반응식
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:15]2[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:35])([CH3:34])[C:16]=2[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1.C(N(CC)C(C)C)(C)C.[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>O1CCCC1.CCOC(C)=O.CCCCCC>[N:45]1([C:5]([NH:13][C:14]2[C:15]3[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:34])([CH3:35])[C:16]=3[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)=[O:11])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

참가 물질

7

반응물 4

HCID 8082PiperidineHCID 81531Diisopropylethylamine2회HCID 94429TriphosgeneHCID 573530855-tert-butyl 1-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

생성물 1

HCID 68649686HCID 68649686, 화합물수율 72%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 21226206Ethyl acetate hexane용매

실험 절차

To a solution of triphosgene (550 mg, 1.85 mmol, 0.4 eq) in tetrahydrofuran (50 ml) was added, at −40° C., a solution of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (1.5 g, 4.62 mmol) in tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (1.8 ml, 2.2 eq). After 3 hours, a solution of piperidine (690 μl, 1.5 eq) and N,N-diisopropylethylamine (1.2 ml, 1.5 eq) in tetrahydrofuran (25 ml) was added. The reaction was allowed to reach room temperature in 2 hours (TLC: EtOAc/hexane 90/10). After evaporation of the solvent the solid was dissolved in DCM and the solution was washed with brine, the organic phase was dried over sodium sulfate and concentrated. The solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50). The solid was treated with diisopropylether and filtered to afford 1.45 g of the title compound in 72% yield.

후처리

  1. waitto reach room temperature in 2 hours
  2. customAfter evaporation of the solvent the solid
  3. dissolutionwas dissolved in DCM
  4. washthe solution was washed with brine
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50)
  8. additionThe solid was treated with diisopropylether
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-f8fc9b06456e4e5fba831db0cd282fcc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557845B2

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