Trifluoroacetic acid → HCID 25123323, compound

HRID 2240947Notes

Reaction equation

HRID 2240947 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[CH:24][CH:23]=3)[C:18](=[O:19])[N:17]([CH3:20])[C:16]([NH2:21])=[N:15]2)[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:21][C:16]1[N:17]([CH3:20])[C:18](=[O:19])[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([NH2:7])[CH:9]=2)([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:30])[F:31])=[CH:24][CH:23]=2)[N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59305350HCID 59305350, compound

Product 1

HCID 25123323HCID 25123323, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

{3-[2-Amino-4-(4-difluoromethoxy-phenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-phenyl}-carbamic acid tert-butyl ester (15.3 g, 34.3 mmol) was dissolved in trifluoroacetic acid/methylene chloride (1:1) (20 mL) and allowed to stir for 4.5 h. Additional trifluoroacetic acid (3.0 mL) was added and the reaction was allowed to stir for an additional hour and concentrated. To the residue was added Na2CO3 followed by extraction with methylene chloride. The organic layer was dried over Na2SO4 and concentrated in vacuo to provide the title compound (11.8 g, 99%), characterized by NMR and mass spectral analyses. MS (ES+) m/e 347 (M+H)+.

Workup

  1. stirringto stir for an additional hour
  2. concentrationconcentrated
  3. additionTo the residue was added Na2CO3
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df14c0a058104efb9309275d3c4dd6fe
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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