Acetone → HCID 57991879, compound

HRID 2075320Notes

Reaction equation

HRID 2075320 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH2:3][NH:4][C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[N:7][N:6]=1.N.[CH3:32][C:33]([CH3:35])=O>CO>[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=1)[CH2:3][NH:4][C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[C:13]3=[C:33]([CH3:35])[CH3:32])=[N:7][N:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 222AmmoniaHCID 56662008HCID 56662008, compound

Product 1

HCID 57991879HCID 57991879, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 2 (5-(5-((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)indolin-2-one) (40 mg, 46 μmol) was dissolved in 1 mL of anhydrous acetone. To the resulting solution was added 2.0 mL of 2.0M ammonia in MeOH. The resulting mixture was stirred for one hour. After removing the solvent, the title compound was obtained as a white solid (20 mg, 48%). LCMS (API-ES) m/z (%): 474.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.45 (s, 3H) 2.59 (s, 3H) 3.06-3.18 (m, 2H) 3.54-3.65 (m, 1H) 3.66-3.76 (m, 1H) 3.86-3.96 (m, 1H) 6.94 (d, J=8.22 Hz, 1H) 7.49-7.57 (m, 3H) 7.62-7.70 (m, 2H) 8.00 (s, 1H).

Workup

  1. customAfter removing the solvent

Sources & evidence

ORD record
ord-a9e5feac22f543e6aba4717d253e0d28
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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