6-(6-{[(1,1-Dimethylethoxy)carbonyl]amino}pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acid → 6-[5-(Hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridine-2-carboxylic acid

HRID 2363744Notes

Reaction equation

HRID 2363744 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([CH:14]=[C:15]([C:17]([O:19]CC)=[O:18])[N:16]=3)[CH:13]=2)=[CH:5][CH:4]=1.CC(C)(OC(NC1N=C(C2C=CC3N(C=C(C(O)=O)N=3)C=2)C=CC=1)=O)C>>[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([CH:14]=[C:15]([C:17]([OH:19])=[O:18])[N:16]=3)[CH:13]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 441249406-(6-{[(1,1-Dimethylethoxy)carbonyl]amino}pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acidHCID 44136209Ethyl 6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 441250776-[5-(Hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridine-2-carboxylic acidYield 95.9%

Procedure

400 mg of ethyl 6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridine-2-carboxylate are saponified under conditions similar to those described for the preparation of Intermediate 11 (step 11.3) to give 346 mg of 6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridine-2-carboxylic acid in the form of a white solid.

Sources & evidence

ORD record
ord-28d3cb764b6440298620093ce2fc8d30
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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