Trifluoroacetic acid → HCID 22633359, compound

HRID 1357651Notes

Reaction equation

HRID 1357651 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:18](OC(C)C)[O:19][CH:20]([CH3:22])[CH3:21])([C:14]([F:17])([F:16])[CH3:15])[C:4]=2[CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH2:18][O:19][CH:20]([CH3:21])[CH3:22])([C:14]([F:16])([F:17])[CH3:15])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 18187329HCID 18187329, compound

Product 1

HCID 22633359HCID 22633359, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Method QQ: To a stirred solution of 7-chloro-5-diisopropoxymethyl-5-(1,1-difluoroethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (53) (360 mg, 0.876 mmol) in anhydrous methylene chloride (4 mL) at room temperature was added trifluoroacetic acid (8 mL) and triethylsilane (6.0 mL, 36.44 mmol). After 14 h at room temperature, the reaction mixture was concentrated in vacuo, the residue was purified by flash chromatography (30%-40% EtOAc-hexane, gradient elution) afforded 55 (248 mg, 80% yield) as a yellow solid (m.p. 148 -149° C.).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (30%-40% EtOAc-hexane, gradient elution)

Sources & evidence

ORD record
ord-41794cab98f447db83bb701b30dc0c21
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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