Trifluoroacetic acid → 7-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamine

HRID 626715Notes

Reaction equation

HRID 626715 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]2=[CH:14][N:15]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[N:16]=[C:12]2[C:11]([Cl:25])=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:11]1[C:12]2[C:13](=[CH:14][N:15]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[N:16]=2)[C:8]([NH2:7])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69671401[7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 696711997-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamineYield 24,845.199%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester (531 mg, contaminated with residual tert-butyl carbamate) and TFA (10 mL) in DCM (10 mL) was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and sodium bicarbonate (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to afford the title compound as a beige solid (100 g, 30% yield over 2 steps). LCMS (Method D): RT=2.15 min, m/z: 313 [M+H+].

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and sodium bicarbonate (sat. aq.)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-65a04e4ba9564b2385d5f51508280b3c
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…