Formic Acid → HCID 20060118, compound

HRID 1085479Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[NH:17][C:16](=[O:18])[NH:15][C:11]3=[N:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.[CH:19](O)=O>>[CH3:19][NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[NH:17][C:16](=[O:18])[NH:15][C:11]3=[N:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 284Formic Acid

HCID 14822879HCID 14822879, compound

Product 1

HCID 20060118HCID 20060118, compound

Procedure

It is contemplated that 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one can be alkylated by reacting it with formic acid followed by reduction of the intermediate formylamino derivative to obtain 6-[4-(methylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one [I; Ar=4-CH3NHC6H4, R1 and R3 =H, R5 =CH3 ]; or by reacting it with formaldehyde under reducing conditions to obtain 6-[4-(dimethylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one [I; Ar=4-(CH3)2NC6H4, R1 and R3 =H, R5 =CH3 ].

Sources & evidence

ORD record: ord-0448b4357bb44c06aa603b8213b88ebe
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05010086

Reaction notes

Loading…