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

HRID 521248
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HRID 521248 반응식
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O-:12])=[O:11])[CH2:6][CH:5]1[F:13])#[N:2].[NH2:14][C:15]1[C:19]([C:20]([NH2:22])=[O:21])=[CH:18][NH:17][N:16]=1.[CH2:23]1[CH2:33][CH2:32]N2C(=NCCC2)CC1.[CH3:34]C#N>CCOC(C)=O>[NH2:14][C:15]1[C:19]([C:20](=[O:21])[NH2:22])=[CH:18][N:17]([C:4]2([CH2:3][C:1]#[N:2])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:33]([CH3:23])([CH3:34])[CH3:32])=[O:11])[CH2:6][CH:5]2[F:13])[N:16]=1
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HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867294264-(Cyanomethylidene)-3-fluoropiperidine-1-carboxylateHCID 178513763HCID 178513763, 화합물

생성물 1

HCID 86729425tert-Butyl 4-(3-amino-4-carbamoyl-1H-pyrazol-1-yl)-4-(cyanomethyl)-3-fluoropiperidine-1-carboxylate

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of tert-butyl (4E and 4Z)-4-(cyanomethylidene)-3-fluoropiperidine-1-carboxylate (800 mg, 3.33 mmol) in MeCN (10 mL) were added 3-amino-1H-pyrazole-4-carboxamide (350 mg, 2.78 mmol) and DBU (0.837 mL, 5.55 mmol). The solution was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with EtOAc and washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The oily residue was purified by MPLC on silica gel (0-100% EtOAc/hexanes) to afford the title compound as a mixture of diastereomers. LRMS (ESI) calc'd for C16H23FN6O3 [M+H]+: 367. Found: 367.

후처리

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by MPLC on silica gel (0-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-2d6d9d7281a248b3bb06502f80e71d1b
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09328099B2

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