Hydrochloric Acid → HCID 117859730, compound

HRID 1486281Notes

Reaction equation

[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH3:21])[C:14]([C:15]([O:17]C)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:22])[CH:7]=1.[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH3:21])[C:14]([C:15]([OH:17])=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:22])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 169 mg (0.43 mmol; about 95% purity) of methyl 7-[(2,6-difluorobenzyl)oxy]-5-methyl-2-propylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 96A in 4.5 ml of dioxane was admixed with 2.6 ml (2.6 mmol) of 1 N sodium hydroxide solution and reacted at 90° C. for 24 h. Subsequently, another 0.5 ml (0.5 mmol) of 1 N sodium hydroxide solution were added and the mixture was stirred at 90° C. for 1 h. The reaction solution was cooled and adjusted to pH 2 with 1 N hydrochloric acid. The solids that precipitated out were filtered off and dried under high vacuum. 180 mg of the title compound (72% by LC-MS, 84% of theory) were obtained and were converted without further purification.

Workup

customreacted at 90° C. for 24 h
temperatureThe reaction solution was cooled
customThe solids that precipitated out
filtrationwere filtered off
customdried under high vacuum

Sources & evidence

ORD record: ord-3e03f1cc94a340349af2cfdcd994075f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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