Acetohydroxamic Acid → HCID 68478268, compound

HRID 2239882Notes

Reaction equation

HRID 2239882 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 68478268HCID 68478268, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-02d753a69abc410db4201d46f37368fb
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

Loading…