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Acetohydroxamic Acid → 6-(8-((4-Methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine

HRID 2239885
Notes
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Reaction equation

HRID 2239885 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1990Acetohydroxamic AcidHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 684836572-Fluoro-4-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile

Product 1

HCID 684838686-(8-((4-Methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

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

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

Sources & evidence

ORD record
ord-6d4ce988d81e4a0dae5929f8a5aa5f33
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723336B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes