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 521211노트

반응식

HRID 521211 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-14bc1986a01744c0b07eb57bf7717367
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328099B2

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