Diisopropylamine → HCID 67432976, 화합물

HRID 1520220

반응식

HRID 1520220 반응식
C([Li])CCC.C(NC(C)C)(C)C.[Li+].CC([N-]C(C)C)C.[CH3:21][O:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][N:28]2[CH:32]=[C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:30]=[N:29]2)=[CH:25][CH:24]=1.CON(C)[C:43]([CH:45]1[CH2:47][CH2:46]1)=[O:44]>C1COCC1.CCOC(C)=O>[CH:45]1([C:43]([C:30]2[C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:32][N:28]([CH2:27][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:39][CH:38]=3)[N:29]=2)=[O:44])[CH2:47][CH2:46]1

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 15643267N-Methoxy-N-methylcyclopropanecarboxamideHCID 44558860ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 67432976HCID 67432976, 화합물수율 9.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

According to Scheme 16: Butyl lithium 2.5 M (9.9 mmol, 4 mL) was added to a solution of diisopropylamine (9.9 mmol, 1.4 mL) in THF (20 mL) at −78° C. and the reaction mixture was stirred at −78° C. for 5 minutes and then at room temperature. To the resulting LDA solution was added at −78° C. a solution of ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (7.61 mmol, 1.98 g) in THF (30 mL) and the reaction mixture was stirred for 15 minutes at −78° C. Then N-methoxy-N-methylcyclopropanecarboxamide (9.14 mmol, 1.18 g) in THF (10 mL) was added and the reaction mixture was stirred at room temperature. The reaction mixture was diluted with AcOEt and washed with a saturated aqueous solution of NH4Cl. The combined organic phases were dried over MgSO4, were filtered and solvents were evaporated. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to yield ethyl 3-(cyclopropanecarbonyl)-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (0.74 mmol, 244 mg, 9%).

후처리

  1. customat room temperature
  2. stirringthe reaction mixture was stirred for 15 minutes at −78° C
  3. stirringthe reaction mixture was stirred at room temperature
  4. washwashed with a saturated aqueous solution of NH4Cl
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationwere filtered
  7. customsolvents were evaporated
  8. customThe crude mixture was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-a7f3b950de5941e197810b8613707ade
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073907B2

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