(E)-4-methylhex-2-enoic Acid → (E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

HRID 333985노트

반응식

HRID 333985 반응식
[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[N:10]1([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CN(C=O)C.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([N:13]1[CH2:14][CH2:15][N:10]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:27])[F:28])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:11][CH2:12]1)=[O:7]

참가 물질

6

반응물 2

HCID 5463168(E)-4-methylhex-2-enoic AcidHCID 114602054-Piperazin-1-yl-7-(trifluoromethyl)quinoline

생성물 1

HCID 86691602(E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 81531Diisopropylethylamine용매2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)용매

실험 절차

(E)-4-Methylhex-2-enoic acid (26 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), HATU was added (76 mg, 0.2 mmol) and the mixture was stirred at room temperature for 15 minutes. 4-piperazin-1-yl-7-(trifluoromethyl)quinoline (56 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), the two solutions were combined and stirred at room temperature overnight. The mixture was evaporated to dryness under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 62.6 mg (0.16 mmol, 80%). MS (APCI) m/z=391.9 [M+1]+.

후처리

  1. additionwas added (76 mg, 0.2 mmol)
  2. stirringstirred at room temperature overnight
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  5. customto yield 62.6 mg (0.16 mmol, 80%)

출처 및 근거

ORD 기록
ord-ffcff14e00e84e19a9757aa08db5402d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

반응 노트

불러오는 중…