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Lithium hydroxide, monohydrate → 4-(2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-methylbenzoic acid

HRID 596083
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596083
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][C:5]([C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)=[CH:4][N:3]=1.O[Li].O>C1COCC1.CO.O>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([CH3:18])[CH:9]=2)=[CH:6][C:5]([C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)=[CH:4][N:3]=1
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Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 118045392methyl 4-(2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-methylbenzoate

Produkt 1

HCID 1180462104-(2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-methylbenzoic acidAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)-2-methylbenzoate (1.20 g, 3.72 mmol) in THF/MeOH/H2O (1:1:1, 36 mL) was added LiOH—H2O (0.234 g, 5.58 mmol). The solution was stirred at room temperature overnight. The pH was adjusted to 3-5, optimally 4. All the organic solvents were removed by reduced pressure. EtOAc was added to triturate out all the impurities. Water was added and the mixture was stirred for 30 min. Solid was filtered and washed well with 50% of ether and water. The solid was then azotropied on rotovap with toluene to provide about 800 mg of desired acid in 69.7% yield. LCMS (m/z): 309.2 (MH+), 0.50 min.

Aufarbeitung

  1. customAll the organic solvents were removed by reduced pressure
  2. additionEtOAc was added
  3. customto triturate out all the impurities
  4. additionWater was added
  5. stirringthe mixture was stirred for 30 min
  6. filtrationSolid was filtered
  7. washwashed well with 50% of ether and water

Quellen und Nachweise

ORD-Eintrag
ord-8cb2b066fbef45379faf8a67275e9ca8
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242996B2

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