Trifluoroacetic acid → HCID 67215727, compound

HRID 1677567Notes

Reaction equation

HRID 1677567 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15](C)[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([C:25]([C:27]3[CH:28]=[CH:29][C:30]([N+:37]([O-:39])=[O:38])=[C:31]([CH:36]=3)[C:32]([O:34][CH3:35])=[O:33])=[O:26])=[N:23][CH:24]=2)[CH:21]=1)=O)(C)(C)C>ClCCl>[CH3:13][NH:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([C:25]([C:27]3[CH:28]=[CH:29][C:30]([N+:37]([O-:39])=[O:38])=[C:31]([CH:36]=3)[C:32]([O:34][CH3:35])=[O:33])=[O:26])=[N:23][CH:24]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67215732HCID 67215732, compound

Product 1

HCID 67215727HCID 67215727, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 ml of trifluoroacetic acid are added to 460 mg (1.01 mmol) of methyl 5-({6-[(tert-butoxycarbonyl)(methyl)amino]imidazo[1,5-a]pyridin-3-yl}carbonyl)-2-nitrobenzoate in 5 ml of dichloromethane and the mixture is stirred at ambient temperature overnight. The reaction medium is concentrated under reduced pressure. The residue is taken up in water and basified with a saturated aqueous sodium bicarbonate solution and then extracted with dichloromethane. The organic phase is washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. 350 mg of a red powder are obtained. Melting point: 183° C.; 1H NMR (d6-DMSO): 2.79 (3H, d), 3.90 (3H, s), 7.11 (1H, d), 7.77 (1H, s), 7.82 (1H, d), 8.31 (1H, d), 8.66 (1H, d), 8.75 (1H, s), 9.01 (1H, s)

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc0e113113df410ca9b2e8ea4a04a8c8
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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