Trifluoroacetic acid → N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1800401노트

반응식

HRID 1800401 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])[N:23]=3)[CH:20]=2)[CH:9]=1)(C)(C)C.COC1C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([N:21]=[C:22]([NH:24][C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[N:23]=2)[CH:20]=1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 91093183Tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate

생성물 1

HCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide수율 83.2%

실험 절차

To a mixture of tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate (1.79 g, 4.39 mmol) and methoxybenzene (0.5 mL) was added trifluoroacetic acid (8.0 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and 5% aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue. The obtained precipitate was collected by filtration, and washed with water, diisopropyl ether and hexane to give the title compound (1.13 g, 83%) as a pale-yellow powder. The obtained compound was used for the next reaction without further purification.

후처리

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 5% aqueous sodium hydrogen carbonate solution (200 mL)
  3. additionwas added to the residue
  4. filtrationThe obtained precipitate was collected by filtration
  5. washwashed with water, diisopropyl ether and hexane

출처 및 근거

ORD 기록
ord-7980237f0886463abbb05cbc663b7ccc
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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