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Acetonitrile → tert-Butyl 4-(3-amino-4-carbamoyl-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate

HRID 1852480
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HRID 1852480 반응식
[NH2:1][C:2]1[C:6]([C:7]([NH2:9])=[O:8])=[CH:5][NH:4][N:3]=1.[C:10]([CH:12]=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)#[N:11].CC#N.C1CCN2C(=NCCC2)CC1>O>[NH2:1][C:2]1[C:6]([C:7](=[O:8])[NH2:9])=[CH:5][N:4]([C:13]2([CH2:12][C:10]#[N:11])[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18]2)[N:3]=1
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참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylateHCID 178513763HCID 178513763, 화합물

생성물 1

HCID 86729368tert-Butyl 4-(3-amino-4-carbamoyl-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 962
Water
용매

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온도
80 °C

실험 절차

3-Amino-1H-pyrazole-4-carboxamide (0.80 g, 6.3 mmol) and tert-butyl 4-(cyanomethylene)piperidine-1-carboxylate (2.1 g, 9.5 mmol) were combined with MeCN (31 mL) in a pressure vessel. DBU (1.05 mL, 6.98 mmol) was then added at ambient temperature. The reaction vessel was sealed and the mixture was heated to 80° C. for 16 hours. The reaction mixture was then allowed to cool to ambient temperature before water (150 mL) was added. The aqueous mixture was extracted with EtOAc (2×). The organic layers were then combined and washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was adsorbed on silica gel in vacuo and purified by MPLC on silica gel (using a gradient elution of 75-100% EtOAc/hexanes) to afford the title compound, Intermediate #47-1.

후처리

  1. customThe reaction vessel was sealed
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by MPLC on silica gel (
  9. washa gradient elution of 75-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-5f901170b76847e48aee9febea70053c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962608B2

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