Sodium Acetate → 6-({2,6-Dichloro-4-[N-ethoxyethanimidoyl]phenyl}amino)pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

HRID 1802509Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]2[C:21]3[CH:22]=[CH:23][NH:24][C:25](=[O:26])[C:20]=3[C:19]3[C:14](=[CH:15][CH:16]=[N:17][CH:18]=3)[N:13]=2)=[C:6]([Cl:27])[CH:5]=1)(=O)[CH3:2].Cl.O[NH:30]CC.[C:33]([O-:36])(=O)[CH3:34].[Na+]>CO>[Cl:27][C:6]1[CH:5]=[C:4]([C:1](=[N:30][O:36][CH2:33][CH3:34])[CH3:2])[CH:9]=[C:8]([Cl:10])[C:7]=1[NH:11][C:12]1[C:21]2[CH:22]=[CH:23][NH:24][C:25](=[O:26])[C:20]=2[C:19]2[C:14](=[CH:15][CH:16]=[N:17][CH:18]=2)[N:13]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-[(4-acetyl-2,6-dichlorophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one (Examples 144 and 145, Step 3) (20 mg, 0.50 mmol) in MeOH (1 mL) was added N-hydroxyethanamine HCl (24 mg, 0.25 Minot) and sodium acetate (21 mg, 0.25 mmol). The solution was heated to 85° C. for 1 hr then cooled to room temperature and extracted with 3:1 CHCl3/iPrOH and water. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (100% CH2Cl2 to 70% CH2Cl2 30% MeOH) provided the product as a mixture of rotamers and E/Z isomers.

Workup

temperaturethen cooled to room temperature
extractionextracted with 3:1 CHCl3/iPrOH and water
dry with materialThe organic layers were dried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by silica gel chromatography (100% CH2Cl2 to 70% CH2Cl2 30% MeOH)
customprovided the product
additionas a mixture of rotamers and E/Z isomers

Sources & evidence

ORD record: ord-927a283afbcd4bc1bf8577b38429e73f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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