Trifluoroacetic acid → HCID 178522973, compound

HRID 606427Notes

Reaction equation

HRID 606427 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]3[N:31]=[CH:30][N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:28]=3)[CH:17]=2)=[O:13])[NH:3]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]3[N:31]=[CH:30][NH:29][N:28]=3)[CH:17]=2)=[O:13])[NH:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1363809674-oxo-N-({3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}propyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide

Product 1

HCID 178522973HCID 178522973, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-oxo-N-({3-[(3-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}propyl)oxy]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 86 (0.285 g, 0.430 mmol) in acetonitrile (6 mL) were added trifluoroacetic acid (1.27 mL) and triethylsilane (0.082 mL, 0.516 mmol) at room temperature, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diethyl ether-EtOH to give the title compound as a white powder (0.173 g, 96%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from diethyl ether-EtOH

Sources & evidence

ORD record
ord-867cf5110cce4c4196d24d3b7b8cc5eb
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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