Triethylamine → 4-(5-Pyridin-4-yl-4H-[1,2,4]triazol-3-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

HRID 221378

반응식

HRID 221378 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16](O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[N:34]1[CH:39]=[CH:38][C:37]([C:40]([NH:42][NH2:43])=[NH:41])=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][C:16]2[NH:41][C:40]([C:37]3[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=3)=[N:42][N:43]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 15020822-((1-((Tert-butoxy)carbonyl)piperidin-4-yl)oxy)acetic acidHCID 5160013N'-aminopyridine-4-carboximidamide

생성물 1

HCID 1784521554-(5-Pyridin-4-yl-4H-[1,2,4]triazol-3-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 4-carboxymethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 1, 255 mg, 0.952 mmol) and triethylamine (138 μl, 0.982 mmol) in toluene was cooled to 0° C. and isobutylchloroformate (127 μl, 0.982 mmol) added. After stirring at rt for 45 min 4-pyridinecarboximidic acid hydrazide (100 mg, 0.82 mmol) and 3 Å powdered molecular sieves (0.82 g) were added and the reaction heated under reflux for 18 h. On cooling, the mixture was filtered through celite, the filtrate evaporated and the residue dissolved in EtOAc (50 ml). After washing with saturated aqueous Na2CO3 (10 ml) and brine (10 ml), the solvent was removed and the residue purified by flash chromatography (EtOAc then 5% MeOH in EtOAc) to afford the title compound: RT=2.81 min; m/z (ES+)=360.1 [M+H]+.

후처리

  1. additionwere added
  2. temperaturethe reaction heated
  3. temperatureunder reflux for 18 h
  4. temperatureOn cooling
  5. filtrationthe mixture was filtered through celite
  6. customthe filtrate evaporated
  7. dissolutionthe residue dissolved in EtOAc (50 ml)
  8. washAfter washing with saturated aqueous Na2CO3 (10 ml) and brine (10 ml)
  9. customthe solvent was removed
  10. customthe residue purified by flash chromatography (EtOAc

출처 및 근거

ORD 기록
ord-630970dab58b4c2883be41289c975ffb
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207147B2

연결된 노트

불러오는 중…