Trifluoroacetic acid → HCID 25051481, compound

HRID 2196426Notes

Reaction equation

HRID 2196426 reaction equation
CC([N:5]([CH2:9][CH:10]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)[CH:15]=1)=[O:12])C(=O)[O-])(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].[NH2:5][CH2:9][CH:10]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)[CH:15]=1)=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642135HCID 86642135, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 25051481HCID 25051481, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl[3-{[3-(1-methyl-1H-pyrazol-5-yl)phenyl]amino}-3-oxo-2-(phenylmethyl)propyl]carbamate (170 mg, 0.39 mmol) was dissolved in DCM (10 mL) and treated with TFA (1 mL). After 1 h, the solution was concentrated and purified using reverse-phase HPLC (C18 column: H2O/CH3CN, 40-10%) affording the bis-TFA salt of the title compound (115 mg, 52%) as a white solid. LC-MS (ES) m/z=335 (M+H)+, 1H NMR (d4-MeOD, 400 MHz) δ 7.76 (br s, 1H), 7.43 (br s, 1 h), 7.35-7.23 (m, 9H), 4.55 (m, 1H), 3.72 (s, 3H), 3.23 (dd, J=3.5, 13.1 Hz, 1H), 3.13 (dd, J=10.4, 13.1 Hz, 1H), and 3.03-2.95 (m, 2H).

Workup

  1. concentrationthe solution was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-539aee8c7b814de897982fb7a512e9de
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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