Acetohydroxamic Acid → HCID 25119286, compound

HRID 2189154Notes

Reaction equation

HRID 2189154 reaction equation
C([NH:4][OH:5])(=O)C.CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH2:34][CH:35]([CH3:37])[CH3:36])[NH:24][C:23](=[O:38])[N:22]=2)=[CH:17][C:14]=1[C:15]#[N:16]>CN(C=O)C>[NH2:16][C:15]1[C:14]2[CH:17]=[C:18]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH2:34][CH:35]([CH3:37])[CH3:36])[NH:24][C:23](=[O:38])[N:22]=3)[CH:19]=[CH:20][C:13]=2[O:5][N:4]=1

Participants

5

Reactant 3

HCID 1990Acetohydroxamic AcidHCID 23665647Potassium tert-butoxideHCID 59363794HCID 59363794, compound

Product 1

HCID 25119286HCID 25119286, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of acetohydroxamic acid (53 mg, 0.7 mmol) in DMF (5 mL) was added potassium tert-butoxide (80 mg, 1.76 mmol). The mixture was stirred at room temperature for 20 min, followed by the addition of solution of 2-fluoro-5-(6-(2-isobutoxyphenyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzonitrile (100 mg, 0.27 mmol) (Example 1, Step 4) in DMF (4 mL). The reaction was stirred at room temperature for 16 h. The mixture was quenched by acid and the product was purified by Prep-HPLC to give 75 mg (74%) of 4-(3-amino-1,2-benzisoxazol-5-yl)-6-{2-[(2-methylpropyl)oxy]phenyl}pyrimidin-2(1H)-one. 1H NMR (400 MHz, d6-DMSO): δ 11.80 (s, br, 2H), 8.78 (s, 1H), 8.37 (d, 1H), 7.66-7.45 (m, 3H), 7.24-7.00 (m, 3H), 6.60 (s, 2H), 3.83 (d, 2H), 2.05-1.97 (m, 1H), 0.98 (d, 6H). MS (EI) for C21H20N4O3: 377 (MH+).

Workup

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. customThe mixture was quenched by acid
  3. customthe product was purified by Prep-HPLC

Sources & evidence

ORD record
ord-6a736afba59b4667b0b02d150e62abe7
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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