Ethyl Acetate → 5-Cyano-2-[2-(3-methyl-isoxazol-5-yl)-acetylamino]-benzoic acid methyl ester

HRID 2053456Notes

Reaction equation

HRID 2053456 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[NH2:12].[CH3:14][C:15]1[CH:19]=[C:18]([CH2:20][C:21](O)=[O:22])[O:17][N:16]=1.CCOC(C)=O>O=P(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[NH:12][C:21](=[O:22])[CH2:20][C:18]1[O:17][N:16]=[C:15]([CH3:14])[CH:19]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acidHCID 10058039METHYL 2-AMINO-5-CYANOBENZOATE

Product 1

HCID 692146715-Cyano-2-[2-(3-methyl-isoxazol-5-yl)-acetylamino]-benzoic acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 2-amino-5-cyano-benzoic acid methyl ester (1.50 g, 8.51 mmol) and (3-methyl-isoxazol-5-yl)-acetic acid (1.32 g, 9.36 mmol) in 40 ml of POCl3 was heated at 80° C. for 2 hr and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H2O (3×40 ml), sat. NaHCO3 (40 ml), brine (40 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure gave 2.31 g (91%) of product as a light yellow solid: 1H-NMR (CDCl3; 400 MHz) δ 11.49 (s, 1H), 8.85 (d, 1H, J=8.8 Hz), 8.35 (d, 1H, J=2.0 Hz), 7.79 (dd, 1H, J=8.8, 2.0 Hz), 6.20 (s, 1H), 3.97 (s, 3H), 3.95 (s, 2H), 2.33 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C15H13N3O4, 300.1 (M+H), found 299.9.

Workup

  1. washthe mixture was washed with H2O (3×40 ml), sat. NaHCO3 (40 ml), brine (40 ml)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-992665b0ad8b41519059a74b696bcc8c
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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