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

HRID 2364579Notes

Reaction equation

HRID 2364579 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), prepared according to Step 1 of Example 8, and CH2Cl2 (20 mL) was added trifluoroacetic acid (7.24 mL, 94.00 mmol). The mixture was stirred at room temperature for 1 h. LCMS showed the product. The mixture was concentrated in vacuo. CH2Cl2 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 and used in next step without purification. m/z=287 (M+1).

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated in vacuo
  3. additionCH2Cl2 was added
  4. customevaporated
  5. customto remove extra TFA
  6. additionEther was added
  7. customevaporated
  8. customThe product was obtained as a yellow oil
  9. customafter drying on vacuum overnight
  10. customused in next step without purification

Sources & evidence

ORD record
ord-bc9ee2eaf3064bca8b76e086272e382e
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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