Trifluoroacetic acid → HCID 18187354, compound

HRID 1357648Notes

Reaction equation

HRID 1357648 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([OH:18])([C:14]([F:17])([F:16])[CH3:15])[C:4]=2[CH:3]=1.[CH:21]1([CH2:24]O)[CH2:23][CH2:22]1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([O:18][CH2:24][CH:21]3[CH2:23][CH2:22]3)([C:14]([F:16])([F:17])[CH3:15])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 75644CyclopropanemethanolHCID 18187342HCID 18187342, compound

Product 1

HCID 18187354HCID 18187354, compoundYield 86.1%

Procedure

Method KK: To a stirred suspension of 7-chloro-5-hydroxy-5-(1,1-difluoroethyl)-5,10-dihydrobenzo[b] [1,8]naphthyridine (37) (173 mg, 0.583 mmol) in cyclopropyl methanol (1.2 mL, 14.58 mmol) was added trifluoroacetic acid (446 μL, 5.83 mmol). The resulting solution was heated at reflux for 3 h 15 min. The reaction mixture was concentrated in vacuo, the residue was purified by flash chromatography (40% EtOAc-hexane) afforded 39 (176 mg, 86% yield) as an off-white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 3 h 15 min
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (40% EtOAc-hexane)

Sources & evidence

ORD record
ord-3c1fb4c5586e4e53a34769c5b431e363
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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