Sodium Hydroxide → 3-(1-{5-[6-(4-Methyl-pyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid

HRID 1716524Notes

Reaction equation

HRID 1716524 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]4[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=4)[N:18]=3)=[CH:15][N:16]=2)[CH2:8][CH2:7]1.[OH-].[Na+]>O1CCCC1.CO>[CH3:30][C:28]1[CH:27]=[CH:26][N:25]=[C:24]([NH:23][C:19]2[N:18]=[C:17]([C:14]3[S:13][C:12]([N:9]4[CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][C:3]([OH:31])=[O:2])[CH2:11][CH2:10]4)=[N:16][CH:15]=3)[CH:22]=[CH:21][CH:20]=2)[CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 587069463-(1-{5-[6(4-Methyl-pyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acid methyl ester

Product 1

HCID 441765793-(1-{5-[6-(4-Methyl-pyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidin-4-yl)propionic acidYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 3-(1-{5-[6-(4-methyl-pyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}piperidine-4-)propionic acid methyl ester (250 mg, 0.57 mmol) obtained in Step 3 in tetrahydrofuran (5 ml) and methanol (5 ml), 4N sodium hydroxide (1.5 ml, 6.0 mmol) was added and the mixture was stirred at room temperature for 12 hours. The concentrate obtained by concentrating the reaction solution in vacuo was neutralized with 0.1N hydrochloric acid, and the precipitated solid was collected by filtration, washed with water and the title compound (142 mg, 59%) was obtained.

Workup

  1. customThe concentrate obtained
  2. concentrationby concentrating the reaction solution in vacuo
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-1222bb7885754c168674955ec2b93ed4
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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