HCID 18419442, compound → HCID 15887619, compound

HRID 635007Notes

Reaction equation

HRID 635007 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22]C(=O)C)=[O:15])=[CH:9][CH:8]=2)=[C:4]([CH3:28])[CH:3]=1>O1CCCC1>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[OH:22])=[CH:9][CH:8]=2)=[C:4]([CH3:28])[CH:3]=1

Participants

3

Reactant 1

HCID 18419442HCID 18419442, compound

Product 1

HCID 15887619HCID 15887619, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

Acetic acid 2-(6-(4-chloro-2-methyl-phenoxy)-pyridin-3-ylcarbamoyl)-phenyl ester (304 mg, 0.77 mmol) dissolved in tetrahydrofuran (3.8 mL) was treated with an aqueous lithium hydrozide solution (1.0 M, 3.8 mL, 3.8 mmol). The solution was stirred for 30 minutes at 22° C. then quenched with aqueous saturated NH4Cl. The mixture was diluted with ethyl acetate then the organics were washed with water, 2× saturated NaHCO3, saturated NaCl, dried over Na2SO4 and concentrated in vacuo. MS (m/z): 354/356 (M+H)+; C19H15N2O3Cl requires 354.8.

Workup

  1. customthen quenched with aqueous saturated NH4Cl
  2. additionThe mixture was diluted with ethyl acetate
  3. washthe organics were washed with water, 2× saturated NaHCO3, saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34496b0e267841a8bf0e65f0afbcb5bd
Source dataset
uspto-grants-2001_02
Patent number
US06184237B2

Reaction notes

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