Trifluoroacetic acid → {3-(5-Chloro-2-difluoromethoxy-phenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acid

HRID 529742Notes

Reaction equation

HRID 529742 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=23)=[O:15])[C:10]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[O:32][CH:33]([F:35])[F:34])=[N:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:31][C:29]1[CH:28]=[CH:27][C:26]([O:32][CH:33]([F:35])[F:34])=[C:25]([C:10]2[C:11]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:12][N:8]([CH2:7][C:6]([OH:36])=[O:5])[N:9]=2)[CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118522636{3-(5-Chloro-2-difluoromethoxyphenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acid tert-butyl ester

Product 1

HCID 118522370{3-(5-Chloro-2-difluoromethoxy-phenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-(5-chloro-2-difluoromethoxyphenyl)-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]pyrazol-1-yl}acetic acid tert-butyl ester (45.0 g, 86.7 mmol) in dichloromethane (350 mL) was added TFA (100 mL) and the mixture left to stir at room temperature for 18 hours. The solvent was evaporated and the resultant residue triturated with diethyl ether. The resultant solid was collected by filtration, washed with diethyl ether and left to air dry to afford the title compound as a white solid (40.0 g, 99%). LCMS (Method 3) [M+H]+=463.1, RT=2.89 min. 1H NMR (400 MHz, CDCl3) δ: (ppm) 9.86 (s, 1H), 8.78 (dd, 1H), 8.71 (s, 1H), 8.56 (dd, 1H), 8.40 (s, 1H), 7.70 (d, 1H), 7.42 (dd, 1H), 7.30 (s, 1H), 6.99 (dd, 1H), 6.47 (t, 1H), 4.86 (s, 2H), 1.49 (s, 9H).

Workup

  1. waitthe mixture left
  2. customThe solvent was evaporated
  3. customthe resultant residue triturated with diethyl ether
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with diethyl ether
  6. waitleft to air
  7. customdry

Sources & evidence

ORD record
ord-5f56ba19614e48118b44e8ce5f902ae4
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

Loading…