3,4-Diaminotoluene → 4-Hydroxy-3-(6-methyl-1H-benzoimidazol-2-yl)-1H-[1,7]naphthyridin-2-one

HRID 2377848Notes

Reaction equation

HRID 2377848 reaction equation
CO[C:3]([CH2:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]([OH:17])=O)=[O:7])=O.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([NH2:26])[CH:20]=1>>[OH:17][C:15]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[NH:8][C:6](=[O:7])[C:5]=1[C:3]1[NH:26][C:21]2[CH:20]=[C:19]([CH3:18])[CH:24]=[CH:23][C:22]=2[N:25]=1

Participants

3

Reactant 2

HCID 103323,4-DiaminotolueneHCID 129887813-[2-(Methoxycarbonyl)acetylamino]pyridine-4-carboxylic acid

Product 1

HCID 1355181534-Hydroxy-3-(6-methyl-1H-benzoimidazol-2-yl)-1H-[1,7]naphthyridin-2-one

Procedure

The title compound was synthesized as described in Example 50 using 3-[2-(methoxycarbonyl)acetylamino]-pyridine-4-carboxylic acid and 4-methyl-1,2-phenylenediamine. The crude product was purified by reversed-phase HPLC (DMSO/5% TFA). LC/MS m/z 293.3 (MH+), Rt 1.99 minutes.

Workup

  1. customThe crude product was purified by reversed-phase HPLC (DMSO/5% TFA)

Sources & evidence

ORD record
ord-5f5eb08ea64e4171a92955412b8c7a7a
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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