Sodium Carbonate → (E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

HRID 333949노트

반응식

HRID 333949 반응식
O[CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6].C(N(S(F)(F)[F:31])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:31][CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2회HCID 86691596(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

생성물 1

HCID 56949080(E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (32.5 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (200 μl) and added to a solution of (diethylamino)sulphur trifluoride (DAST; 19 μl, 0.12 mmol) in 200 μl dichloromethane. The mixture was stirred for 30 minutes at room temperature, additional DAST was added (10 μl, 0.063 mmol) and stirring was continued for additional 30 minutes. Solid sodium carbonate (25 mg) was added, the mixture was filtered, the filtrate evaporated to dryness and the residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 4 mg (0.012 mmol, 12%).

후처리

  1. stirringstirring
  2. waitwas continued for additional 30 minutes
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customthe residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  6. customto yield 4 mg (0.012 mmol, 12%)

출처 및 근거

ORD 기록
ord-6bf75af861a74a5d9256c2e2ffcf0118
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

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