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Triethylamine → Tert-butyl 4-(4-(1-(pyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

HRID 873567
노트
인쇄 미리보기

반응식

HRID 873567 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:11][CH:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.C1CC=CCC=1>[Pd]>[N:7]1[CH:2]=[CH:3][CH:4]=[C:5]([N:8]2[CH2:11][CH:10]([C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([CH:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]4)=[CH:19][CH:20]=3)=[O:13])[CH2:9]2)[N:6]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 123431,4-CyclohexadieneHCID 86702042Tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

생성물 1

HCID 86702044Tert-butyl 4-(4-(1-(pyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
80 °C

실험 절차

To a 50 mL round-bottomed flask was added tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate (550 mg, 1.165 mmol) and Pd/C (93 mg, 0.087 mmol). The flask was flushed with nitrogen for 10 minutes and ethanol (11.7 ml) was added. Triethylamine (0.162 ml, 1.165 mmol) and cyclohexa-1,4-diene (654 mg, 8.16 mmol) were added and the reaction was stirred at 80° C. for 1 hour, cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue was purified by regular phase flash column chromatography to give the title compound.

후처리

  1. customThe flask was flushed with nitrogen for 10 minutes
  2. additionethanol (11.7 ml) was added
  3. temperaturecooled
  4. filtrationfiltered through diatomaceous earth
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by regular phase flash column chromatography

출처 및 근거

ORD 기록
ord-a82ea6b1561f4fc09794abf23a3a08cc
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975398B2

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