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

HRID 1852480
ノート
印刷プレビュー

反応式

HRID 1852480 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5f901170b76847e48aee9febea70053c
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962608B2

反応ノート

読み込み中…

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