6-[(4-acetyl-2,6-dichlorophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one → 6-{[2,6-Dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

HRID 1802491Notes

Reaction equation

HRID 1802491 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:3])[CH3:2].[CH3:28][Mg]Br>C1COCC1>[Cl:27][C:6]1[CH:5]=[C:4]([C:1]([OH:3])([CH3:28])[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

4

Reactant 2

HCID 594359706-[(4-acetyl-2,6-dichlorophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 594361096-{[2,6-Dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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) (1.3 g, 3.26 mmol) in THF (30 mL) at 0° C. under nitrogen atmosphere was added methyl magnesium bromide (11.6 mL, 1.4 M in THF/toluene) and the reaction mixture stirred for 30 min. The solution was quenched with 1 N citric acid, diluted with 1:1 THF/EtOAc, and neutralized with saturated NaHCO3. The organic layer was concentrated, triturated with diethyl ether, and filtered to afford the desired product as a yellow powder.

Workup

  1. customThe solution was quenched with 1 N citric acid
  2. additiondiluted with 1:1 THF/EtOAc
  3. concentrationThe organic layer was concentrated
  4. customtriturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-304d54e347644a7b875be7c00561e21b
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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