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Oxalyl chloride → Methyl 2-[1-(2-methyl-4-quinolyl)-4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-2-yl]acetate

HRID 333983
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HRID 333983 반응식
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH3:16][C:17]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH:28]2[CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:16][C:17]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:29][CH:28]2[CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 66835808Methyl 2-[1-(2-methyl-4-quinolyl)piperazin-2-yl]acetate

생성물 1

HCID 66836038Methyl 2-[1-(2-methyl-4-quinolyl)-4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-2-yl]acetate

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
2회
HCID 6344Dichloromethane용매

실험 절차

(E)-4,4,4-Trifluorobut-2-enoic acid (15.4 mg, 0.08 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (9.4 μl, 0.11 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. Methyl 2-[1-(2-methyl-4-quinolyl)piperazin-2-yl]acetate (33.6 mg, 0.1 mmol) was dissolved in DMF (1 ml) together with diisopropylethylamine (44 μl, 0.25 mmol), the solutions were combined and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 3.9 mg (0.0093 mmol, 9%).

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  4. customto yield 3.9 mg (0.0093 mmol, 9%)

출처 및 근거

ORD 기록
ord-dd90ecebe18949c88a1ffafc59729ca2
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883791B2

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