O-Phenylenediamine → 3-(1H-benzo[d]imidazol-2-yl)-4-hydroxy-1,7-naphthyridin-2(1H)-one

HRID 1170010Notes

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

Participants

Reactant 2

HCID 7243O-Phenylenediamine

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

Product 1

HCID 1354102863-(1H-benzo[d]imidazol-2-yl)-4-hydroxy-1,7-naphthyridin-2(1H)-one

Conditions

Temperature: 150 °C

Procedure

3-[2-(Methoxycarbonyl)acetylamino]pyridine-4-carboxylic Acid (1.1 equivalents) was combined with 1,2-phenylenediamine (1.0 equivalent) and heated at 150° C. for 3 hours. The crude product was purified by reversed-phase HPLC (DMSO/5% TFA). LC/MS m/z 279.3 (MH+), Rt 1.73 minutes.

Workup

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

Sources & evidence

ORD record: ord-a9089f7e2082430684c171ed95ec7dc0
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825132B2

Reaction notes

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