Trifluoroacetic acid → HCID 58654424, compound

HRID 1170538Notes

Reaction equation

HRID 1170538 reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:13]2[N:18]=[C:17]([CH:19]3[CH:23]([C:24](=[O:27])[NH:25][CH3:26])[CH2:22][CH2:21][N:20]3C(OC(C)(C)C)=O)[CH:16]=[C:15]([CH3:35])[N:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[N:8]1([C:13]2[N:18]=[C:17]([CH:19]3[CH:23]([C:24]([NH:25][CH3:26])=[O:27])[CH2:22][CH2:21][NH:20]3)[CH:16]=[C:15]([CH3:35])[N:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58654334HCID 58654334, compound

Product 1

HCID 58654424HCID 58654424, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (20.0 mL, 269 mmol) was added dropwise over 5 minutes to a 0° C. solution of tert-butyl 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-(methylcarbamoyl)pyrrolidine-1-carboxylate (720 mg, 1.86 mmol) in CH2Cl2 (20 mL). The reaction mixture was warmed to rt over 30 minutes then brought to pH=8 with Na2CO3 (400 mL, sat. aqueous solution). The mixture was extracted with CH2Cl2 (5×30 mL), the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-N-methylpyrrolidine-3-carboxamide (230 mg, 43%) as a yellow oil.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (5×30 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12912190070f4151bd9aed9a47a8eea1
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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