Trifluoroacetic acid → HCID 118522581, compound

HRID 529744Notes

Reaction equation

HRID 529744 reaction equation
C([O:5][C:6](=[O:44])[CH2:7][N:8]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:17]([NH:25]C(OC(C)(C)C)=O)=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[N:21][C:20]=23)=[O:15])[C:10]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[O:40][CH:41]([F:43])[F:42])=[N:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:25][C:17]1[C:16]([C:14]([NH:13][C:11]2[C:10]([C:33]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=3[O:40][CH:41]([F:42])[F:43])=[N:9][N:8]([CH2:7][C:6]([OH:44])=[O:5])[CH:12]=2)=[O:15])=[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][N:19]2[N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118522632HCID 118522632, compound

Product 1

HCID 118522581HCID 118522581, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-[(2-tert-butoxycarbonylamino-pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-3-(5-chloro-2-difluoromethoxy-phenyl)-pyrazol-1-yl]-acetic acid tert-butyl ester (0.91 g, 1.43 mmol) in dichloromethane (7 mL) was added TFA (15 mL) and the mixture left to stir at room temperature for 6 hours. The solvent was evaporated and the resultant residue azeotroped with dichlormethane/methanol to afford the title compound as a pale yellow solid (0.66 g, 97%). LCMS (Method 3) [M+H]+=477.8, RT=2.95 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 13.15 (br s, 1H), 9.56 (s, 1H), 8.93 (dd, 1H, J=1.5, 6.8 Hz), 8.37-8.34 (m, 1H), 8.35 (s, 1H), 7.63 (dd, 1H, J=2.8, 8.8 Hz), 7.56 (d, 1H, J=2.8 Hz), 7.46 (d, 1H, J=8.9 Hz), 7.26 (t, 1H, J=73.4 Hz), 7.00 (dd, 1H, J=4.5, 6.8 Hz), 6.58 (br s, 2H), 5.05 (s, 2H).

Workup

  1. waitthe mixture left
  2. customThe solvent was evaporated
  3. customthe resultant residue azeotroped with dichlormethane/methanol

Sources & evidence

ORD record
ord-93a38fcdc2c64e15a134b2b04017b4e1
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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