Hydrochloric Acid → HCID 25227126, compound

HRID 1802459Notes

Reaction equation

HRID 1802459 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:28])=[C:9]([NH:11][C:12]2[C:21]3[C:16](=[C:17](Cl)[N:18]=[CH:19][CH:20]=3)[C:15]3[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:14]=3[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=[O:31].[Na+]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:28])=[C:9]([NH:11][C:12]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:31])[C:16]=3[C:15]3[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:14]=3[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59436103N-(5-tert-Butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-amine

Product 1

HCID 25227126HCID 25227126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-tert-butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthridin-5-amine (110 mg, 0.28 mmol) was taken up in THF (3.5 mL) and 6 N HCl (3.5 mL) and heated to 85° C. for 2 hr. The reaction was cooled to room temperature, neutralized with saturated NaHCO3 and extracted with EtOAc. The organic layers were dried over Mg2SO4, filtered, and concentrated. Column chromatography on silica gel (100% hexane to 100% EtOAc) provided the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Mg2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bbae645fa5c4700a714cda29533945f
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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