Acetohydroxamic Acid → HCID 68478268, Verbindung

HRID 2239882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239882
C([NH:4][OH:5])(=O)C.CC(C)([O-])C.[K+].C1COCC1.F[C:18]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]([N:35]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[N:31]=2)=[CH:22][C:19]=1[C:20]#[N:21]>CN(C=O)C.CO>[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([CH2:42][N:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:28]2[C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[N:31]=[C:26]([C:23]3[CH:24]=[CH:25][C:18]4[O:5][N:4]=[C:20]([NH2:21])[C:19]=4[CH:22]=3)[CH:27]=2)=[CH:48][CH:47]=1

Komponenten

7

Edukt 4

HCID 1990Acetohydroxamic AcidHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 684836932-Fluoro-5-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile

Produkt 1

HCID 68478268HCID 68478268, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of acetohydroxamic acid (42 mg, 0.556 mmol) in DMF (1 mL) was added a solution of potassium t-butoxide in THF (0.56 mL, 0.56 mmol). The reaction solution was stirred at RT for 15 minutes and then a solution of 2-fluoro-5-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile (25 mg, 0.056 mmol) from (1b) in DMF (1 mL) was added. The reaction solution was stirred at RT for 24 hours. The solution was diluted with methanol and purified by preparative HPLC to give 5-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine. LC/MS, m/e 463 (M+1). HPLC Rt, 3.13 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min. hold at 100% B 1 min, flow rate 4 mL/min.

Aufarbeitung

  1. stirringThe reaction solution was stirred at RT for 24 hours
  2. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-02d753a69abc410db4201d46f37368fb
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723336B2

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