Trifluoroacetic acid → HCID 90411374, compound

HRID 1850680Notes

Reaction equation

HRID 1850680 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N:21]2[CH2:26][CH2:25][CH:24]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:23][CH2:22]2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N:21]2[CH2:22][CH2:23][CH:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732451HCID 131732451, compound

Product 1

HCID 90411374HCID 90411374, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 1-[4-[(2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]-3-pyridyl]piperidine-4-carboxylate trifluoroacetic acetate (prepared according to a methodology similar to the one described in Example 1) (101 mg, 0.1773 mmol) in DCM (5 mL) was added TFA (1 mL, 12.98 mmol). The mixture was stirred at room temperature for 20 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and diethyl ether (×2) to give title compound as a beige solid (98% Yield, di-TFA salt). 1H NMR (500 MHz, DMSO) δ 11.10 (s, 1H), 9.58 (dd, 1H), 8.91 (d, 1H), 8.86 (d, 1H), 8.68 (s, 1H), 8.56 (d, 1H), 6.92 (s, 2H), 3.10 (d, 2H), 2.99-2.82 (m, 2H), 2.53-2.50 (m, 1H), 2.15-1.93 (m, 4H); 19F NMR (471 MHz, DMSO) δ −74.10, −151.83; LC-MS ES+: 400.0.

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. customthe residue azeotroped with DCM (×2) and diethyl ether (×2)

Sources & evidence

ORD record
ord-f85a41b2c803401c8e42fcf3e1b089c8
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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