Water → HCID 59370342, compound

HRID 1848617Notes

Reaction equation

HRID 1848617 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:20]1[CH:21]=[N:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=1.C([O-])([O-])=[O:29].[K+].[K+].CCOC(C)=O.O>C1COCC1.[Li+].[OH-]>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[O:7])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([NH2:27])=[O:29])=[N:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86642575HCID 86642575, compound

Product 1

HCID 59370342HCID 59370342, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(6-cyano-pyridin-3-yl)-N-(2-methoxy-phenyl)-N-methyl-benzamide 2-2 (29 mg, 0.077 mmol) in THF (0.5 mL), 1N LiOH (0.5 mL) and K2CO3 (10 mg, 0.073 mmol) were added. After stirring for 48 hrs at room temperature, EtOAc and water were added. The aqueous layer was removed and the organic layer was concentrated, dissolved in MeOH and subjected to preparative LCMS to yield 5-{2-chloro-5-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-pyridine-2-carboxylic acid amide 24-1. MS (M+H)+: 396.0, tR=5.93 min (method 2).

Workup

  1. customThe aqueous layer was removed
  2. concentrationthe organic layer was concentrated
  3. dissolutiondissolved in MeOH

Sources & evidence

ORD record
ord-a1d523205da44c2380f0f3ef74b54bfd
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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