Acetohydroxamic Acid → 6-(8-((4-Methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine
Reaction equation
C([NH:4][OH:5])(=O)C.CC(C)([O-])C.[K+].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1.F[C:18]1[CH:25]=[C:24]([C:26]2[CH:27]=[C:28]([N:35]([CH2:42][C:43]3C=CC(OC)=[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:23]=[CH:22][C:19]=1[C:20]#[N:21]>CN(C=O)C.CO>[CH3:14][O:15][C:16]1[CH:12]=[CH:13][C:43]([CH2:42][N:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:28]2[C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[N:31]=[C:26]([C:24]3[CH:23]=[CH:22][C:19]4[C:20]([NH2:21])=[N:4][O:5][C:18]=4[CH:25]=3)[CH:27]=2)=[CH:44][CH:45]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of acetohydroxamic acid (50 mg, 0.667 mmol) in DMF (1 mL) was added a solution of potassium t-butoxide in THF (0.667 mL, 0.667 mmol). The reaction solution was stirred at RT for 15 minutes and then a solution of 2-fluoro-4-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile (30 mg, 0.067 mmol) from (X) 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 6-(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, 3.08 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.
Workup
- stirringThe reaction solution was stirred at RT for 24 hours
- custompurified by preparative HPLC
Sources & evidence
- ORD record
- ord-6d4ce988d81e4a0dae5929f8a5aa5f33
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723336B2
Reaction notes
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