Piperidine → HCID 68649686、化合物

HRID 1626280ノート

反応式

HRID 1626280 の反応式
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

参加物

7

反応物 4

HCID 8082PiperidineHCID 81531Diisopropylethylamine2 回HCID 94429TriphosgeneHCID 573530855-tert-butyl 1-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

生成物 1

HCID 68649686HCID 68649686、化合物収率 72%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f73f13af6cc40ffa81e2b84ade75e51
出典データセット
uspto-grants-2014_07
特許番号
US08785448B2

反応ノート

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