Pivaloyl chloride → Ethyl 5-(2,2-dimethylpropanoyl)-3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate

HRID 1042384노트

반응식

HRID 1042384 반응식
Cl.[F:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]3[CH2:22][NH:21][C:20]([CH3:24])([CH3:23])[C:12]=3[N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38].CCOC(C)=O.CCCCCC>ClCCl>[CH3:38][C:37]([CH3:40])([CH3:39])[C:36]([N:21]1[CH2:22][C:11]2[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:26][CH:25]=3)=[N:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12]=2[C:20]1([CH3:23])[CH3:24])=[O:41]

참가 물질

6

반응물 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 68649268Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride

생성물 1

HCID 68649346Ethyl 5-(2,2-dimethylpropanoyl)-3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride (2.0 g, 5.77 mmol) in dichloromethane (70 ml) was treated, at 0° C., with N,N-diisopropylethylamine (1.6 ml, 9.2 mmol, 1.6 eq) and with pivaloyl chloride (780 μL, 6.3 mmol, 1.1 eq). Gradually, the reaction was brought to room temperature and stirred overnight (TLC: CH2Cl2/EtOAc 90/10). The solution was washed with saturated sodium hydrogencarbonate aqueous solution and brine. The organic phase was dried over sodium sulfate, evaporated and purified by flash chromatography (eluent: CH2Cl2/EtOAc 90/10) to afford 2.03 g of the title compound in 82% yield.

후처리

  1. customwas brought to room temperature
  2. washThe solution was washed with saturated sodium hydrogencarbonate aqueous solution and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. custompurified by flash chromatography (eluent: CH2Cl2/EtOAc 90/10)

출처 및 근거

ORD 기록
ord-2d05e6d64d684f82b85e5442121cf10f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557845B2

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