Diethyl Pyrocarbonate → 1-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide

HRID 1479846노트

반응식

HRID 1479846 반응식
[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:4]1([C:7]([OH:9])=O)[CH2:6][CH2:5]1)[CH3:2].CCOC(OC(OCC)=O)=O.[F:31][C:32]([F:48])([F:47])[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[C:43]([CH2:45][NH2:46])[CH:42]=[CH:41][N:40]=2)=[CH:35][CH:34]=1>C1COCC1>[CH2:1]([N:3]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:4]1([C:7]([NH:46][CH2:45][C:43]2[CH:42]=[CH:41][N:40]=[C:39]([C:36]3[CH:37]=[CH:38][C:33]([C:32]([F:48])([F:31])[F:47])=[CH:34][CH:35]=3)[CH:44]=2)=[O:9])[CH2:5][CH2:6]1)[CH3:2]

참가 물질

5

반응물 3

HCID 3051Diethyl PyrocarbonateHCID 68758847[2-(4-Trifluoromethyl-phenyl)-pyridin-4-yl]methylamineHCID 903843631-[Ethyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylic acid

생성물 1

HCID 903841851-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide수율 26.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Acid 15A (303 mg, 1 mmol) was dissolved in 5 ml of THF and at rt DEPC (1.1 equiv, 0.17 ml) and [2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 21A (1.1 equiv., 277.5 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. he residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (1:1 EtOAc:Petroleum ether) afforded 140 mg of a white solid. Yield=26.8% 1HNMR (DMSO, 400 MHz) δ 1.09 (2H, bs), 1.23 (3H, t, J=7.2 Hz), 1.40 (2H, bs), 3.40 (2H, q, J=6.8 Hz), 4.41 (2H, bs), 7.26 (1H, dd), 7.42 (2H, t, J=8.8 Hz), 7.87 (4H, m), 7.98 (1H, bs), 8.30 (3H, bd), 8.64 (1H, dd, J=4.8 Hz) [M+1] 521.9 (C25H23F4N3O3S requires 521.53).

후처리

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionhe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (1:1 EtOAc:Petroleum ether)

출처 및 근거

ORD 기록
ord-40b66184ffaf4aba94adb4a358c76b95
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

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