Hydrochloric Acid → 6-[(4-acetyl-2,6-dichlorophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

HRID 1802490Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:13])OCC[O:9]2)[CH:5]=[C:4]([Cl:14])[C:3]=1[NH:15][C:16]1[C:25]2[CH:26]=[CH:27][N:28]=[C:29]([O:30]CC)[C:24]=2[C:23]2[C:18](=[CH:19][CH:20]=[N:21][CH:22]=2)[N:17]=1.ClC1C=C(C2(C)OCCO2)C=C(Cl)C=1NC1C2C=CN=C(OC)C=2C2C(=CC=NC=2)N=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([Cl:14])[C:3]([NH:15][C:16]2[C:25]3[CH:26]=[CH:27][NH:28][C:29](=[O:30])[C:24]=3[C:23]3[C:18](=[CH:19][CH:20]=[N:21][CH:22]=3)[N:17]=2)=[C:2]([Cl:1])[CH:7]=1)(=[O:9])[CH3:13]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of N-[2,6-dichloro-4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine and N-[2,6-dichloro-4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-10-methoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (3.0 g) in THF (30 mL) was added 6 N HCl (20 mL) and the mixture was heated to 85° C. for 3.5 hr. After cooling to room temperature, the mixture was neutralized with saturated NaHCO3 and extracted with 1:1 THF/EtOAc. The precipitate between the organic and aqueous layers were collected and determined to be pure by LCMS. The organic layer was concentrated and purified by column chromatography (100% CH2Cl2 to 30% MeOH).

Workup

temperatureAfter cooling to room temperature
extractionextracted with 1:1 THF/EtOAc
customThe precipitate between the organic and aqueous layers were collected
concentrationThe organic layer was concentrated
custompurified by column chromatography (100% CH2Cl2 to 30% MeOH)

Sources & evidence

ORD record: ord-7d2c5dcaae7e439bb17e2db13ce3f10c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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