Trifluoroacetic acid → HCID 67116173, compound

HRID 1524901Notes

Reaction equation

HRID 1524901 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([C:16](=[O:29])[C:17]3[C:22]([N:23]4[N:27]=[CH:26][CH:25]=[N:24]4)=[CH:21][CH:20]=[CH:19][C:18]=3[F:28])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:28][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([N:23]2[N:27]=[CH:26][CH:25]=[N:24]2)[C:17]=1[C:16]([N:12]1[CH2:13][CH:14]2[CH:10]([CH2:9][NH:8][CH2:15]2)[CH2:11]1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671161965-(2-Fluoro-6-[1,2,3]triazol-2-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

Product 1

HCID 67116173HCID 67116173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-Fluoro-6-[1,2,3]triazol-2-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (1.3 g, 3.21 mmol) was taken up in DCM (6.0 mL) and TFA (3.0 mL) was added. The mixture was allowed to stir at rt for 1 hr. Solvent was removed and then taken back up in DCM and basified with 1N aq. NaOH. The layers were separated. The aqueous was extracted 2 more time with DCM (and a small amount of MeOH). The organics were combined, dried (Na2SO4), filtered, and concentrated to provide the desired free base product, (2-fluoro-6-[1,2,3]triazol-2-yl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone, as a viscous/foamy residue that was found to be very hydroscopic (950.6 mg, 93.3%). MS (ESI): mass calculated for C15H16FN5O, 301.32, m/z found 302.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.90-7.73 (m, 3H), 7.54-7.42 (m, 1H), 7.19-7.10 (m, 1H), 3.85-2.65 (m, 10H).

Workup

  1. customSolvent was removed
  2. customThe layers were separated
  3. extractionThe aqueous was extracted 2 more time with DCM (and a small amount of MeOH)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3277ae7f27d1470c9600f662f433821d
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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