Trifluoroacetic acid → HCID 136052346, compound

HRID 1889478Notes

Reaction equation

HRID 1889478 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([CH2:16][CH3:17])[S:15][C:9]=2[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]1=[O:37].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:16]([C:14]1[S:15][C:9]2[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][C:34](=[O:36])[O:33][N:32]=4)=[CH:21][CH:20]=3)[C:7](=[O:37])[NH:6][C:11](=[O:12])[C:10]=2[CH:13]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136052260HCID 136052260, compound

Product 1

HCID 136052346HCID 136052346, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2,4-dimethoxybenzyl)-6-ethyl-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.3 g) and trifluoroacetic acid (5 mL) was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (10 mL), and the mixture was concentrated under reduced pressure. The obtained residue was dissolved in 1N aqueous sodium hydroxide solution, washed with chloroform, and adjusted to pH 4 with 1N hydrochloric acid. The precipitated solid was collected by filtration to give the title compound as colorless crystals (0.21 g, 93%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in 1N aqueous sodium hydroxide solution
  3. washwashed with chloroform
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-35667194fe62439ea5647a24ba69f1f2
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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