Trifluoroacetic acid → HCID 86636680, compound

HRID 2075408Notes

Reaction equation

HRID 2075408 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[O:8]=[C:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[S:22][C:21]([CH2:23][CH2:24][C@@H:25]([NH:37]C(=O)OC(C)(C)C)[CH2:26][C:27]4[CH:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=4)=[N:20][N:19]=3)[CH:15]=2)[NH:10]1>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[NH2:37][C@@H:25]([CH2:26][C:27]1[CH:28]=[N:29][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:31][CH:32]=1)[CH2:24][CH2:23][C:21]1[S:22][C:18]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:8])[CH2:17]3)=[N:19][N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86636679HCID 86636679, compound

Product 1

HCID 86636680HCID 86636680, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl (R)-4-(5-(2-oxoindolin-5-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (185 mg, 347 μmol) in DCM (2 mL), and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting yellow oil was purified by reversed phase HPLC (Shimadsu Valiant, Phenomenex Gemini C18 5 μm 100×30 mm, 10% to 70% H2O/MeCN, 0.1% TFA) to provide 5-(5-((R)-3-amino-4-(6-(trifluoromethyl)pyridin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)indolin-2-one trifluoroacetate as a white solid (38 mg, 88%). LCMS (API-ES) m/z: 434.0 (M+H+); 1H NMR (300 MHz, CD3OD) δ ppm 2.24 (q, J=7.4 Hz, 2 H), 3.12 (dd, J=14.3, 7.4 Hz, 1 H), 3.24 (dd, J=14.3, 6.7 Hz, 1 H), 3.33-3.40 (m, 2 H), 3.61 (s, 2 H), 3.78 (quin, J=6.7 Hz, 1 H), 7.01 (d, J=8.0 Hz, 1 H), 7.76-7.83 (m, 2 H), 8.01 (dd, J=8.0, 1.1 Hz, 1 H), 8.68 (d, J=1.1 Hz, 1 H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting yellow oil was purified by reversed phase HPLC (Shimadsu Valiant, Phenomenex Gemini C18 5 μm 100×30 mm, 10% to 70% H2O/MeCN, 0.1% TFA)

Sources & evidence

ORD record
ord-feb42589fa48478589ba66d93e9883fe
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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