Trifluoroacetic acid → HCID 178509494, compound

HRID 606393Notes

Reaction equation

HRID 606393 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24][C:25]([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)=[O:26])[CH:18]=1)=[O:14])[NH:7][C:6]2=[O:51])#[N:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24][C:25]([C:27]3[N:31]=[CH:30][NH:29][N:28]=3)=[O:26])[CH:18]=1)=[O:14])[NH:7][C:6]2=[O:51])#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136380969HCID 136380969, compound

Product 1

HCID 178509494HCID 178509494, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-cyano-4-oxo-N-({3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)methyl]phenyl}methyl)-3,4-dihydroquinazoline-2-carboxamide (420 mg, 0.626 mmol), triethylsilane (0.105 mL, 0.657 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 (113 mg, 42%).

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-ae79f3c87d9f4d919d3f014237e680bf
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

Loading…