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Sodium Carbonate → (+/-)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-methoxy-5,6-dihydropyrazin-2(1H)-one

HRID 576720
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HRID 576720 반응식
[Cl:1][C:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][NH:8][C:7](=[O:14])[C:6]1=[O:15].[C:24](=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.C([O+](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:12][CH2:13]2)[CH2:9][N:8]=[C:7]([O:14][CH3:24])[C:6]1=[O:15]
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 90402584(+-)-1-(2-Chloro-3-(trifluoromethyl)benzyl)-6-cyclopropylpiperazine-2,3-dione

생성물 1

HCID 90402452(+/-)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-methoxy-5,6-dihydropyrazin-2(1H)-one수율 100%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To an ice cooled solution of Intermediate 5 (400 mg, 1.2 mmol) and sodium carbonate (2.5 g, 23 mmol) in DCM (45 mL) was added triethyloxonium tetrafluoroborate (1M in DCM, 5.8 mL, 5.8 mmol) dropwise. The ice bath was removed and the reaction was stirred at rt for 1.5 h. Water was added and the mixture was extracted with DCM (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a yellow oil (432 mg, 100%), which was used directly without further purification. MS (ESI): mass calcd. for C17H18ClF3N2O2, 374.1; m/z found, 375.1 [M+H]+.

후처리

  1. customThe ice bath was removed
  2. additionWater was added
  3. extractionthe mixture was extracted with DCM (×3)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6b34399b80a94b2ba68963421fae9baf
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040534B2

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