1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 4-[4-carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidine-1-carboxylate

HRID 521211ノート

反応式

HRID 521211 の反応式
[C:1]1([NH:7][C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][NH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([CH:18]=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)#[N:17].C1CCN2C(=NCCC2)CC1>C(#N)C.O>[C:13]([C:12]1[C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:9][N:10]([C:19]2([CH2:18][C:16]#[N:17])[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:23][CH2:24]2)[CH:11]=1)(=[O:14])[NH2:15]

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylateHCID 178513764HCID 178513764、化合物

生成物 1

HCID 71536247tert-Butyl 4-[4-carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 3-(phenylamino)-1H-pyrazole-4-carboxamide, Intermediate 31-1, (1.4 g, 6.9 mmol) and tert-butyl 4-(cyanomethylidene)piperidine-1-carboxylate, Intermediate 19-1 (3.1 g, 13.8 mmol) in acetonitrile (23 mL) was added DBU (1.0 mL, 6.9 mmol), and maintained at ambient temperature for 18 hours. The mixture was diluted with water, extracted with EtOAc, and the combined organics were washed with brine, dried over anhydrous MgSO4, and filtered. The filtrate was adsorbed onto silica gel in vacuo and then purified by MPLC on silica gel (using a gradient elution of 0-80% EtOAc/DCM) to afford the title compound, Example #2-1.

後処理

  1. extractionextracted with EtOAc
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. custompurified by MPLC on silica gel (
  6. washa gradient elution of 0-80% EtOAc/DCM)

出典と根拠

ORDレコード
ord-14bc1986a01744c0b07eb57bf7717367
出典データセット
uspto-grants-2016_05
特許番号
US09328099B2

反応ノート

読み込み中…