Hydrochloric Acid → 4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-piperidine-1-carboxylic acid benzyl ester

HRID 572085

반응식

HRID 572085 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][NH2:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24].Cl>CCO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:23]([NH2:24])=[CH:22][C:21]([C:20]([CH3:27])([CH3:26])[CH3:19])=[N:18]2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 21098319Benzyl 4-hydrazinylpiperidine-1-carboxylate

생성물 1

HCID 866866934-(5-Amino-3-tert-butyl-pyrazol-1-yl)-piperidine-1-carboxylic acid benzyl ester수율 21.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A yellow solution of Intermediate 16a (1.80 g, 7.22 mmol), 4,4-dimethyl-3-oxopentanenitrile (1.08 g, 8.66 mmol), and HCl (4M in dioxane, 2.70 mL, 10.8 mmol) in EtOH (25 mL) was stirred at reflux for 4 h. The cooled solution was applied to an SCX-2 cartridge (50 g), washed with MeOH (100 mL). The product was eluted with 2M NH3 in MeOH (100 mL); concentration in vacuo left a yellow oil (772 mg). FCC, using 0-5% MeOH in DCM, gave the title compound as a yellow gum (550 mg, 21%). LCMS (Method 3): Rt 2.88 min, m/z 357 [MH+].

후처리

  1. temperatureat reflux for 4 h
  2. washwashed with MeOH (100 mL)
  3. washThe product was eluted with 2M NH3 in MeOH (100 mL)
  4. concentrationconcentration in vacuo
  5. waitleft a yellow oil (772 mg)

출처 및 근거

ORD 기록
ord-2d879c92bf56452c9b37bfa612d2d97a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029373B2

연결된 노트

불러오는 중…