Hydrochloric Acid → HCID 21712141, compound

HRID 650501Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]2[C:13]([Cl:14])=[CH:12][C:11]([F:15])=[C:10]([C:16]3[C:20]([Cl:21])=[C:19]([O:22][CH:23]([F:25])[F:24])[N:18]([CH3:26])[N:17]=3)[N:9]2[CH:27]=1)=[O:5])C.[OH-].[Na+].Cl>CS(C)=O>[Cl:14][C:13]1[C:8]2[N:9]([CH:27]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[C:10]([C:16]2[C:20]([Cl:21])=[C:19]([O:22][CH:23]([F:25])[F:24])[N:18]([CH3:26])[N:17]=2)=[C:11]([F:15])[CH:12]=1

Participants

Conditions

Temperature: 22 °C

Procedure

0.51 g of 8-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-[1H]-pyrazol-3-yl)-6-fluoro-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (Example P58) is dissolved in 3 ml of dimethyl sulfoxide and, with cooling in an ice-bath, 0.63 ml of a 2N aqueous sodium hydroxide solution is added. The mixture is then stirred for 1 hour at 22° C. Because the TLC analysis of a worked-up sample indicates that starting material is still present, a further 0.1 ml of 2N sodium hydroxide solution is added. After subsequently stirring for 30 minutes, the mixture is rendered strongly acidic with dilute hydrochloric acid, the resulting slurry is filtered, and the filtration residue is subsequently washed with cold water and dried in vacuo at 50° C. 0.35 g of the desired title compound is obtained in the form of a white solid (crude product).

Workup

temperaturewith cooling in an ice-bath
stirringAfter subsequently stirring for 30 minutes
filtrationthe resulting slurry is filtered
washthe filtration residue is subsequently washed with cold water
customdried in vacuo at 50° C

Sources & evidence

ORD record: ord-cbc089b17b5a4fc089afcf11ee12f47f
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274536B1

Reaction notes

Loading…