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

HRID 576720
Notes
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Reaction equation

HRID 576720 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-6b34399b80a94b2ba68963421fae9baf
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040534B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes