Hydrochloric Acid → HCID 86732061, compound

HRID 1498797Notes

Reaction equation

HRID 1498797 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]([O:19]CC)=[O:18])[CH:11]=[C:10]([CH3:22])[N:9]=2)[N:3]=1.[Li+].[OH-].Cl>O1CCCC1.CO.O>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]([OH:19])=[O:18])[CH:11]=[C:10]([CH3:22])[N:9]=2)[N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86732060HCID 86732060, compound

Product 1

HCID 86732061HCID 86732061, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl trans-2-(2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-4-yl)cyclopropanecarboxylate (25-2, 96 mg, 0.320 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added a solution of LiOH (38 mg, 1.60 mmol) in water (2 mL). The mixture was stirred at room temperature for 3 hours, neutralized with 2 M HCl to pH 7, and concentrated. The residue was purified by silica gel column chromatography (0-8% methanol in DCM) to give trans-2-(2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-4-yl)cyclopropanecarboxylic acid (25-3) as a white solid. LRMS m/z (M+H) 273 found, 273 required.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (0-8% methanol in DCM)

Sources & evidence

ORD record
ord-3bc3c12f8376469a9b18c4e80140bc10
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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