Trifluoroacetic acid → 4-(3-(Azetidin-3-YL)pyrazin-2-YL)-2-fluoro-N-methylbenzamide tris(2,2,2-trifluoroacetate)

HRID 2364585Notes

Reaction equation

HRID 2364585 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]([CH:18]3[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)=[N:14][CH:15]=[CH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:11])[NH:9][CH3:10].[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>C(Cl)Cl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[NH:20]1[CH2:19][CH:18]([C:13]2[C:12]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([NH:9][CH3:10])=[O:11])=[C:2]([F:1])[CH:3]=3)=[N:17][CH:16]=[CH:15][N:14]=2)[CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705405Tert-butyl 3-(3-(3-fluoro-4-(methylcarbamoyl)phenyl)pyrazin-2-YL)azetidine-1-carboxylate

Product 1

HCID 867054064-(3-(Azetidin-3-YL)pyrazin-2-YL)-2-fluoro-N-methylbenzamide tris(2,2,2-trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 3-(3-(3-fluoro-4-(methylcarbamoyl)phenyl)pyrazin-2-yl)azetidine-1-carboxylate (5.19 g, 13.43 mmol) and DCM (20 mL) was added 2,2,2-trifluoroacetic acid (7.24 mL, 94 mmol). The mixture was stirred at rt for 1 h. The mixture was concentrated in vacuo. DCM was added and evaporated to remove extra TFA. Ether was added and evaporated. The product was obtained as a yellow oil after drying on vacuum overnight. MS: 287 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionDCM was added
  3. customevaporated
  4. customto remove extra TFA
  5. additionEther was added
  6. customevaporated
  7. customThe product was obtained as a yellow oil
  8. customafter drying on vacuum overnight

Sources & evidence

ORD record
ord-699a4d1993ec4c30ba773a251cd71bfc
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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