Trifluoroacetic acid → HCID 135599892, compound

HRID 1175803Notes

Reaction equation

HRID 1175803 reaction equation
[NH2:1][C:2]1[N:3]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8](CC3C=CC(OC)=CC=3)[C:7](=[O:24])[C:6]=12.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>>[NH2:1][C:2]1[N:3]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:24])[C:6]=12

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 23153869HCID 23153869, compound

Product 1

HCID 135599892HCID 135599892, compoundYield 94.1%

Procedure

A mixture of 3-amino-5-(4-methoxybenzyl)-2-(2-methoxyphenyl)-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (370 mg), anisole (2 ml), trifluoroacetic acid (5 ml) and trifluoromethanesulfonic acid (1 ml) was stirred at room temperature for 3.5 hours. The mixture was concentrated under reduced pressure. To the mixture was added 5% sodium carbonate to adjust pH to about 9. Ethyl acetate was added to the mixture. An insoluble solid was collected by filtration, washed with water and ethyl acetate, and dried to obtain the target compound (250 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionTo the mixture was added 5% sodium carbonate
  3. additionEthyl acetate was added to the mixture
  4. filtrationAn insoluble solid was collected by filtration
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-02259c02da8647fa8effa619bff0b8e7
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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