Hydrochloric Acid → 2-Methyl-2-(1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid

HRID 1716528Notes

Reaction equation

HRID 1716528 reaction equation
C([O:3][C:4](=[O:33])[C:5]([CH3:32])([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=4)[N:19]=3)=[CH:16][N:17]=2)[CH2:9][CH2:8]1)[CH3:6])C.[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:32][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=4)[N:19]=3)=[CH:16][N:17]=2)[CH2:9][CH2:8]1)([CH3:6])[C:4]([OH:33])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 587067352-Methyl-2-(1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid ethyl ester

Product 1

HCID 441766832-Methyl-2-(1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acidYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 2-methyl-2-(1-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid ethyl ester (697 mg, 1.50 mmol) obtained in Step 3 in methanol (5 ml) and tetrahydrofuran (10 ml), 4N aqueous sodium hydroxide (3.7 ml, 15 mmol) was added and the mixture was stirred for 15 hours under refluxing. After concentrated, the reaction solution was neutralized with 1N hydrochloric acid (15 ml, 15 mmol), and the precipitated solid was collected by filtration, washed with water, ethyl acetate, tetrahydrofuran. After dried in vacuo, the title compound (438 mg, 67%) was obtained.

Workup

  1. temperatureunder refluxing
  2. concentrationAfter concentrated
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water, ethyl acetate, tetrahydrofuran
  5. customAfter dried in vacuo

Sources & evidence

ORD record
ord-26fc5a5b0a19465595cbb08041ca5aa1
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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