O-Phenylenediamine → 2,3-Dihydro-4-[2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-yl]-1H-[1,5]benzodiazepin-2-one

HRID 1085129Notes

Reaction equation

HRID 1085129 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[CH3:9][C:10]1[N:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH2:27][C:28](OCC)=[O:29])=O)=[CH:21][N:20]=2)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1>>[CH3:9][C:10]1[N:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH2:27][C:28](=[O:29])[NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[N:1]=3)=[CH:21][N:20]=2)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 54245582Ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate

Product 1

HCID 200610162,3-Dihydro-4-[2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-yl]-1H-[1,5]benzodiazepin-2-oneYield 14.3%

Procedure

The procedure of Example 1 was followed using 1,2-diaminobenzene (86 mg, 0.76 mmol) and ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate (260 mg, 0.80 mmol). The crude product was purified by flash chromatography (eluting with ethyl acetate/methanol =6:1), followed by recrystallisation from acetone to give the title compound (40 mg, 14%) as a buff solid, m.p. 208°-210° C..

Workup

  1. customThe crude product was purified by flash chromatography (eluting with ethyl acetate/methanol =6:1)
  2. customfollowed by recrystallisation from acetone

Sources & evidence

ORD record
ord-9da3c3e866134fd3a5229327fbad55e8
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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