Trifluoroacetic acid → Trifluoroacetic acid

HRID 1961307Notes

Reaction equation

HRID 1961307 reaction equation
CC([N:5]([CH2:9][CH:10]([NH:18][C:19]([C:21]1[S:22][CH:23]=[C:24]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[C:25]=1[CH3:26])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)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]([NH:18][C:19]([C:21]1[S:22][CH:23]=[C:24]([C:27]2[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=2)[C:25]=1[CH3:26])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633569HCID 86633569, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 57826397HCID 57826397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[2-({[3-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (51 mg, 0.11 mmol) in DCM (1 mL) was added TFA (1 mL). The reaction was stirred over 5 h, concentrated and purified by reverse-phase HPLC (C18 column: H2O/CH3CN, 40-10%) to afford the bis-TFA salt of the title compound. (16 mg, 41%): LC-MS (ES) m/z 355 (M+H)+. NMR (d4-MeOD, 400 MHz) δ ppm 7.64 (s, 1H), 7.56 (d, J=1.8 Hz, 1H), 7.36-7.30 (m, 4H), 7.28-7.21 (m, 1H), 6.30 (d, J=2.0 Hz, 1H), 4.58 (m, 1H), 3.69 (s, 3H), 3.27-3.13 (m, 2H), 3.07-2.93 (m, 2H), and 2.13 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC (C18 column: H2O/CH3CN, 40-10%)

Sources & evidence

ORD record
ord-f70d7305f2b1484a9b6f92af20d3841d
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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