Trifluoroacetic acid → HCID 178431869, compound

HRID 606395Notes

Reaction equation

HRID 606395 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]([C:26]4[N:30]=[CH:29][N:28](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:27]=4)=[O:25])[CH:17]=3)=[O:13])=[N:6][C:5]=2[S:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]([C:26]4[N:30]=[CH:29][NH:28][N:27]=4)=[O:25])[CH:17]=3)=[O:13])=[N:6][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 667692035-methyl-4-oxo-N-({3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)methyl]phenyl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Product 1

HCID 178431869HCID 178431869, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methyl-4-oxo-N-({3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)methyl]phenyl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide (565.0 mg, 0.849 mmol), triethylsilane (0.142 mL, 0.891 mmol) and trifluoroacetic acid (3 mL) in dichloromethane (10 mL) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from IPE. The obtained powder was suspended in ethanol, and the suspension was stirred under heating for 2 hr to give the title compound as a white powder (359 mg, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from IPE
  3. temperatureunder heating for 2 hr

Sources & evidence

ORD record
ord-58fcf8d9efb648f198ca9ab51091edc9
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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