HCID 10904968, compound → HCID 22626712, compound

HRID 277965Notes

Reaction equation

HRID 277965 reaction equation
FC(F)(F)C([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[S:23][CH3:24])=O>CO.C(Cl)Cl>[NH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[C:22]=1[S:23][CH3:24]

Participants

3

Reactant 1

HCID 10904968HCID 10904968, compound

Product 1

HCID 22626712HCID 22626712, compoundYield 850%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The 2-trifluoroacetamido-3-methylthio-6-benzoyl-imidazo[1,2-a]pyridine (100 mg, 263 mmol) was dissolved in 20 mL of a mixture of MeOH/CH2Cl2 1:1, and 5 g of silica gel was added. The mixture was stirred at RT for 2 days. The residue was filtered and washed with CH2Cl2 and the solution was concentrated in vacuo to give 63 mg (850%) of a yellow solid. 1H-NMR (200 MHz, CDCl3) d 2.12 (s, 3H, SMe), 4.40 (bs, 2H, NH2), 7.46-7.80 (m, 7H, ArH+H7+H8), 8.68 (d, J57=1.7, H5). 13C-NMR (50 MHz, CDCl3) d 18.0 (SMe), 95.0, 122.7, 125.8, 127.7, 128.5, 129.6, 132.6, 137.4, 145.3, 156.1, 193.5.

Workup

  1. additionwas added
  2. filtrationThe residue was filtered
  3. washwashed with CH2Cl2
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-791548bf603146f18dbd7f09c509d391
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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