Hydrochloric Acid → HCID 59436026, compound

HRID 1802473Notes

Reaction equation

HRID 1802473 reaction equation
[Br:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([NH:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([C:24]4([CH3:29])OCC[O:25]4)=[CH:19][C:18]=3[Cl:30])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:14]C)[N:11]=[CH:10][CH:9]=3.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[C:24]([C:20]1[CH:19]=[C:18]([Cl:30])[C:17]([NH:16][C:7]2[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]3[CH:3]=[C:2]([Br:1])[CH:32]=[CH:31][C:5]=3[N:6]=2)=[C:22]([Cl:23])[CH:21]=1)(=[O:25])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59436102HCID 59436102, compound

Product 1

HCID 59436026HCID 59436026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 9-bromo-N-[2,6-dichloro-4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-1-methoxybenzo[c]-2,6-naphthyridin-5-amine (1.40 g, 2.62 mmol) in THF (24 mL) was added 6 N HCl (8mL) and the reaction mixture was heated to 85° C. for 45 min. The solution was cooled to room temperature and neutralized with sat. NaHCO3. The mixture was extracted with a mixture of 1:3 iPrOH/CHCl3. The organic layers were combined, dried over MgSO4, filtered, and concentrated to afford the title compound.

Workup

  1. extractionThe mixture was extracted with a mixture of 1:3 iPrOH/CHCl3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eed78b4d857f46b6ab87d13674e6c841
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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