Trifluoroacetic acid → HCID 21874960, compound

HRID 2110490Notes

Reaction equation

HRID 2110490 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]2[N:10]([N:16]=[CH:17][CH:18]=2)[C:11]([C:14]#[N:15])=[CH:12][CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[C:9]2[N:10]([N:16]=[CH:17][CH:18]=2)[C:11]([C:14]#[N:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58746070HCID 58746070, compound

Product 1

HCID 21874960HCID 21874960, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a clear solution of (7-cyano-pyrazolo[1,5-a]pyridin-4-yl)-carbamic acid tert-butyl ester (3 g, 11.6 mmol) in methylene chloride (40 mL) was added TFA (8 mL). The mixture was stirred at rt for 3 h, and then concentrated under reduced pressure. The residue was partitioned between EtOAc (100 mL) and sat. NaHCO3 solution (50 mL). The aqueous solution was separated and extracted with EtOAc (2×50 mL). The combined organic solutions were dried over Na2SO4, filtered though SiO2 pad, and concentrated under reduced pressure. Crystallization in EtOAc and 95% EtOH gave compound 777F (1.07 g, 58%) as a dark yellow solid. HPLC: 97% at 1.96 min (retention time) (YMC S5 ODS-A column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 mincontaining 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 159 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc (100 mL) and sat. NaHCO3 solution (50 mL)
  3. customThe aqueous solution was separated
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic solutions were dried over Na2SO4
  6. filtrationfiltered though SiO2 pad
  7. concentrationconcentrated under reduced pressure
  8. customCrystallization in EtOAc

Sources & evidence

ORD record
ord-5eb0cb060d7441448881f01503377187
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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