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Hydrochloric Acid → 2-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486282
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1486282
[CH:1]1([C:4]2[C:23]([C:24]([O:26]C)=[O:25])=[C:7]3[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=4[F:21])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1>[CH:1]1([C:4]2[C:23]([C:24]([OH:26])=[O:25])=[C:7]3[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=4[F:21])[N:6]3[N:5]=2)[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117859596Methyl 2-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Produkt 1

HCID 1178596452-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylic AcidAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 384 mg (1.02 mmol) of methyl 2-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 99A in 10.6 ml of dioxane was admixed with 10.2 ml (10.2 mmol) of 1 N sodium hydroxide solution and the mixture was stirred at 100° C. for 7 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. The filtrate was admixed once again with 1 N hydrochloric acid. The solids that precipitated out were filtered off and dried under high vacuum together with the previously isolated solids. A total of 361 mg of the title compound (74% by LC-MS, 73% of theory) were obtained and were converted without further purification.

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. customThe solids that precipitated out
  3. filtrationwere filtered off
  4. customdried under high vacuum
  5. customThe solids that precipitated out
  6. filtrationwere filtered off
  7. customdried under high vacuum together with the previously isolated solids

Quellen und Nachweise

ORD-Eintrag
ord-c3f445d7fa774bd0ac08e418de1d41eb
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09422285B2

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