HCID 18187295, compound → HCID 18187362, compound

HRID 1357646Notes

Reaction equation

HRID 1357646 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[C:13]2[CH:16]([F:18])[F:17])[CH:11]=[CH:10][CH:9]=[N:8]3)=[CH:4][CH:3]=1.[CH2:19]([Li])[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH2:19]([C:13]1([CH:16]([F:18])[F:17])[C:12]2[CH:11]=[CH:10][CH:9]=[N:8][C:7]=2[NH:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][C:14]1=2)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 18187295HCID 18187295, compoundHCID 178418339Butyllithium

Product 1

HCID 18187362HCID 18187362, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Method GG: A solution of 7-chloro-9-difluoromethyl-4-azaacridine (396 mg 1.5 mmol) in THF (10 mL) was cooled under N2 to −78° C. n-Butyl lithium was added dropwise over 15 min and the reaction mixture was stirred at −78° C. for 5 h. The reaction was quenched with sat. NH4Cl solution and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried and concentrated. Column chromatography (SiO2, 10% EtOAc-hexane-1% Et3N) afforded the desired material 5-Butyl-7-chloro-5-difluoromethyl-5,10-dihydro-benzo[b][1,8]naphthyridine as a viscous yellow oil (10 mg, 2.1%).

Workup

  1. additionwas added dropwise over 15 min
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb9d22ff006f4e8ea58e48d161c20d2b
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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