Trifluoroacetic acid → 1-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)urea

HRID 408864노트

반응식

HRID 408864 반응식
[CH:1]1([CH2:4][NH:5][C:6](=[O:29])[NH:7][C:8]2[CH:28]=[CH:27][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])=[CH:27][CH:28]=2)=[O:29])[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58055802tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazine-1-carboxylate

생성물 1

HCID 580558061-(Cyclopropylmethyl)-3-(4-(Piperazine-1-carbonyl)phenyl)urea수율 94.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)benzoyl)piperazine-1-carboxylate (46.7 mmol, 18.78 g) was dissolved in dichloromethane (30 mL) and trifluoroacetic acid (233 mmol, 17.33 ml, 26.6 g) was added. The reaction was stirred for 1 hour and then was concentrated under reduced pressure. The crude material was triturated with ether to give a white powder after high vacuum drying. The white powder was taken up in water and carefully taken to pH 10 with sodium carbonate. The aqueous was then extracted with dichloromethane and the combined organic phases were dried, filtered and concentrated under reduced pressure to give the title compound (13.4 g).

후처리

  1. concentrationwas concentrated under reduced pressure
  2. customThe crude material was triturated with ether
  3. customto give a white powder after high vacuum
  4. customdrying
  5. extractionThe aqueous was then extracted with dichloromethane
  6. customthe combined organic phases were dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e94b7fe153794c769b3b30cead44d5c1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759352B2

반응 노트

불러오는 중…