1,1'-Carbonyldiimidazole → N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-1H-imidazole-1-carboxamide

HRID 2061159Notes

Reaction equation

HRID 2061159 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([CH3:18])[CH:12]=3)[CH:7]=1.[CH:22]1[N:26]=[CH:25][N:24]([C:27](N2C=NC=C2)=[O:28])[CH:23]=1>C(#N)C>[CH3:19][N:10]1[C:11]2[C:16](=[CH:15][N:14]=[C:13]([CH3:18])[CH:12]=2)[CH:17]=[C:8]([C:6]2[CH:7]=[C:2]([NH:1][C:27]([N:24]3[CH:23]=[CH:22][N:26]=[CH:25]3)=[O:28])[CH:3]=[CH:4][C:5]=2[CH3:21])[C:9]1=[O:20]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 592123103-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 58368998N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-1H-imidazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 15 (22 mg, 0.08 mmol) in ACN (0.5 mL) was added CDI (16 mg, 0.09 mmol). After stirring at rt for 2 h, solvent was removed and the crude N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-1H-imidazole-1-carboxamide 18 was used without further purification. MS m/z 374.3 (M+1).

Workup

  1. customsolvent was removed
  2. customthe crude N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-1H-imidazole-1-carboxamide 18 was used without further purification

Sources & evidence

ORD record
ord-20205dbe794f40158a372ff53ed1cf6c
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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