Trifluoroacetic acid → HCID 56662008, compound

HRID 2075318Notes

Reaction equation

HRID 2075318 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]3[S:15][C:14]([NH:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[N:13][N:12]=3)[CH:8]=2)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=1)[CH2:17][NH:16][C:14]1[S:15][C:11]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH2:10]3)=[N:12][N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57991909HCID 57991909, compound

Product 1

HCID 56662008HCID 56662008, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (S)-1-(5-(2-oxoindolin-5-yl)-1,3,4-thiadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (350 mg) and TFA (10 mL) in DCM (10 mL) was stirred at room temperature for 1 hour. The solvent was removed under vacuum. The residue was partitioned between saturated sodium bicarbonate and DCM. The combined organic portions were washed with brine and then dried over sodium sulfate. Removal of the solvent gave the title compound 5-(5-((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)indolin-2-one as an off-white amorphous solid (137 mgs, 48%). LCMS (API-ES) m/z (%): 434.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 3.05-3.16 (m, 2H) 3.54-3.64 (m, 3H) 3.68-3.76 (m, 1H) 3.90 (td, J=7.14, 4.30 Hz, 1H) 6.96 (d, J=8.22 Hz, 1H) 7.54 (d, J=8.02 Hz, 2H) 7.60-7.65 (m, 1H) 7.65-7.71 (m, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was partitioned between saturated sodium bicarbonate and DCM
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-8299332d42674a99b23d7b8a524deda6
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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