HCID 18187347, compound → HCID 18187285, compound

HRID 1357655Notes

Reaction equation

HRID 1357655 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:23]([F:25])[F:24])([CH:14](OC(C)C)[O:15][CH:16]([CH3:18])[CH3:17])[C:4]=2[CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:23]([F:24])[F:25])([CH2:14][O:15][CH:16]([CH3:18])[CH3:17])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 18187347HCID 18187347, compound

Product 1

HCID 18187285HCID 18187285, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Method NNN To a stirred solution 7-chloro-5-(difluoromethyl)-5-diisopropoxymethyl-5,10-dihydrobenzo[b][1,8]naphthyridine (94) (50 mg, 0.13 mmol) in trifluoroacetic acid (2 mL) at room temperature was added borane-methyl sulfide complex (36 μL, 0.38 mmol). After 14 h at room temperature, the reaction mixture was quenched with 1.0 N NaOH and extracted with EtOAc (3×). The combined layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow residue was taken up in MeOH (3 mL), acidified with 4 N HCl in dioxane (100 μL), and stirred at room temperature for 3 hours. The solution was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue afforded 95 in quantitative yield.

Workup

  1. customthe reaction mixture was quenched with 1.0 N NaOH
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe solution was quenched with saturated aqueous NaHCO3 (50 mL)
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee91f75066cc446a84d9f2ebf53a58a7
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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