Trifluoroacetic acid → HCID 67215444, compound

HRID 1677564Notes

Reaction equation

HRID 1677564 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:15]([C:17]1[N:21]2[CH:22]=[C:23]([C:26]([O:28]C(C)(C)C)=[O:27])[CH:24]=[CH:25][C:20]2=[CH:19][N:18]=1)=[O:16])=[O:11]>ClCCl.CC(C)=O>[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:15]([C:17]1[N:21]2[CH:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=[CH:25][C:20]2=[CH:19][N:18]=1)=[O:16])=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67216035HCID 67216035, compound

Product 1

HCID 67215444HCID 67215444, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

2.13 ml (28.68 mmol) of trifluoroacetic acid are added to 610 mg (1.43 mmol) of tert-butyl 3-[3-(methoxycarbonyl)-4-nitrobenzoyl]imidazo[1,5-a]pyridine-6-carboxylate in 2 ml of dichloromethane and the mixture is stirred at ambient temperature for 5 hours. The reaction medium is concentrated under reduced pressure and then the residue obtained is taken up in acetone. The precipitate formed is filtered off, washed with acetone and dried. 450 mg of a yellow powder are obtained. Melting point: 290° C.; 1H NMR (d6-DMSO): 3.90 (3H, s), 7.78 (1H, d), 8.04 (1H, s), 8.12 (1H, d), 8.26 (1H, d), 8.68 (1H, d), 8.75 (1H, s), 10.26 (1H, s)

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customthe residue obtained
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-40d5726db1b349e2bd23ccc7d753ea27
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

Loading…