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Hydrochloric Acid → 5-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 908224
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 908224
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([CH3:32])[C:12]=1[C:13](=[O:31])[NH:14][C:15]1[C:20]([Br:21])=[CH:19][N:18]2[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=[C:17]2[CH:16]=1)=[O:7])C.O.Cl>C1COCC1.CO>[Br:21][C:20]1[C:15]([NH:14][C:13]([C:12]2[N:11]([CH3:32])[N:10]=[CH:9][C:8]=2[C:6]([OH:7])=[O:5])=[O:31])=[CH:16][C:17]2[N:18]([CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:24]=2)[CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 670422785-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 670416185-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaOH (3N, 0.65 ml) was added to a solution of 5-(6-bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (460 mg, 0.98 mmol) in a mixture of THF (5 ml) and methanol (5 ml), and the reaction mixture was stirred at r.t. overnight. An additional amount of NaOH (3N, 0.65 ml) and water (2 ml) were added and the mixture was heated to reflux (1 h). After cooling to r.t., HCl (conc., ˜0.7 ml) was added to the cooled mixture, and the brown suspension was stirred at r.t. (15 min). The suspension was then filtered, and the precipitated title compound (150 mg, 35%) was washed with a small amount of water, dried under vacuum, and used in the next step without further purification. MS (m/e)=440.3 [M+H+].

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux (1 h)
  3. temperatureAfter cooling to r.t.
  4. stirringthe brown suspension was stirred at r.t. (15 min)
  5. filtrationThe suspension was then filtered
  6. customthe precipitated title compound (150 mg, 35%)
  7. washwas washed with a small amount of water
  8. customdried under vacuum
  9. customused in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a3fd6c37535b4bf0bd5fd18f22ae793f
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017604B2

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