Trifluoroacetic acid → HCID 118045003, compound

HRID 525760Notes

Reaction equation

HRID 525760 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]([F:53])([F:52])[O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[CH:21]=[C:22]([C:41]3[N:45](C4CCCCO4)[N:44]=[CH:43][CH:42]=3)[C:23]([N:26]3[CH2:30][CH2:29][C:28]([CH2:32][NH:33]C(=O)OC(C)(C)C)([OH:31])[CH2:27]3)=[N:24][CH:25]=2)=[O:19])=[CH:13][CH:12]=1>C(Cl)Cl>[NH2:33][CH2:32][C:28]1([OH:31])[CH2:29][CH2:30][N:26]([C:23]2[C:22]([C:41]3[NH:45][N:44]=[CH:43][CH:42]=3)=[CH:21][C:20]([C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([O:10][C:9]([Cl:8])([F:52])[F:53])=[CH:16][CH:15]=3)=[O:19])=[CH:25][N:24]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118053785HCID 118053785, compound

Product 1

HCID 118045003HCID 118045003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.288 mL, 3.74 mmol) was added to a solution of tert-butyl ((1-(5-((4-(chlorodifluoromethoxy)phenyl)carbamoyl)-3-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-2-yl)-3-hydroxypyrrolidin-3-yl)methyl)carbamate (Stage 83.1, 74 mg, 0.112 mmol) in DCM (0.6 mL) and the RM was stirred at RT for 4 h. The solvent was evaporated off under reduced pressure and the crude product was purified by preparative HPLC. The fractions containing pure product were combined, the TFA was removed using a PL HCO3-MP cartridge and the solvent was evaporated off under reduced pressure to afford the title compound as a beige solid. UPLC-MS (Condition 8) tR=0.78 min, m/z=479.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.87 (m, 2H) 2.59 (s, 2H) 3.07 (s, 1H) 3.16-3.48 (m, 3H) 4.74 (br. s, 1H) 6.39 (d, J=1.83 Hz, 1H) 7.34 (d, J=8.93 Hz, 2H) 7.67-7.88 (m, 1H) 7.90 (s, 2H) 8.04 (d, J=2.32 Hz, 1H) 8.74 (s, 1H) 10.20 (s, 1H) 12.93 (br. s, 1H).

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe crude product was purified by preparative HPLC
  3. additionThe fractions containing pure product
  4. customthe TFA was removed
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-06340229517d4c838856dff6003d7ee6
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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