Methanol → HCID 44159846, compound

HRID 1894694Notes

Reaction equation

HRID 1894694 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[C:9]([NH:14]C(=O)C(C)(C)C)=[N:10][CH:11]=[CH:12][CH:13]=2)[O:5][N:4]=1.CO.[OH-].[Na+]>C(O)(=O)C>[NH2:14][C:9]1[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][OH:1])[CH:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57867417HCID 57867417, compound

Product 1

HCID 44159846HCID 44159846, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
58.5 °C

Procedure

To a mixture of N-{3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}-2,2 dimethylpropanamide (82.8 g) obtained in Reference Example 9 and methanol (350 mL) was added 5N aqueous sodium hydroxide (350 mL) at room temperature, which was stirred at 57 to 60° C. for 14 hours. To the reaction mixture was added acetic acid (100 mL) and the precipitated solid was filtered to obtain the title compound (42.2 g) as a grayish white solid.

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-13e6f4b19838490ab2e497435179da4b
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

Loading…