Water → HCID 59370342, compound

HRID 1485972Notes

Reaction equation

HRID 1485972 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-a4a4821fb22b4492899ff2d5e26a70f0
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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