Acetic Acid → 2,2-dimethyl-3-({4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzyl}amino)propan-1-ol

HRID 1920034

Reaktionsgleichung

Reaktionsgleichung von HRID 1920034
[C:1]1([C:7]2[C:8]([C:22]3[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[C:14]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)[N:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:30][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1>[CH3:35][C:32]([CH3:36])([CH2:31][NH:30][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([C:8]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[N:13][C:14]=3[C:17]3[CH:21]=[N:20][NH:19][CH:18]=3)[N:9]=2)=[CH:29][CH:28]=1)[CH2:33][OH:34]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57500726HCID 57500726, Verbindung

Produkt 1

HCID 468939922,2-dimethyl-3-({4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzyl}amino)propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a solution of 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde (1-3) (0.11 g, 0.29 mmol) in NMP (10 mL) was added 3-amino-2,2-dimethylpropan-1-ol (0.030 g, 0.29 mmol) and acetic acid (0.026 g, 0.43 mmol). After stirring at room temperature for 2 hours, sodium triacetoxyborohydride (0.092 g, 0.43 mmol) was added and the reaction was stirred at room temperature for 15 hours. The reaction was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. Purification by reverse phase chromatography (5-95% acetonitrile/water/0.1% TFA; Water Sunfire C18) gave 2,2-dimethyl-3-({4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzyl}amino)propan-1-ol (1-4) as a off white solid. HRMS (M+H)+: calculated 464.2207; found 464.2194

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 15 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by reverse phase chromatography (5-95% acetonitrile/water/0.1% TFA; Water Sunfire C18)

Quellen und Nachweise

ORD-Eintrag
ord-d36c234d7aa2479d862e35a3df0624f2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168652B2

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