[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid tert-butyl ester → [5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid

HRID 1992636Notes

Reaction equation

HRID 1992636 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:13]=1)(C)(C)C>Cl.O1CCOCC1>[CH3:20][N:17]1[CH2:18][CH2:19][N:14]([C:12]2[CH:13]=[C:8]([CH2:7][C:6]([OH:21])=[O:5])[CH:9]=[N:10][CH:11]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 66869311[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid tert-butyl ester

Product 1

HCID 66869047[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

[5-(4-Methyl-piperazin-1-yl)-pyridin-3-yl]-acetic acid tert-butyl ester (1.68 g, 5.77 mmol) is dissolved in 4 M HCl in dioxane (28 ml). After 1 h at 60° C., TLC analysis indicated complete consumption of starting material. The reaction mixture is cooled to RT and diluted with Et2O. The precipitate is filtered and washed with Et2O to yield the title compound, which is used in the next reaction without further purification. 1H NMR (d6-DMSO 400 MHz): δ 2.79 (s, 3H), 3.05-4.10 (br m, 8H), 3.81 (s, 2H), 8.04 (s, 1H), 8.22 (s, 1H), 8.45 (s, 1H). ES+−MS: 236.4 [M+H]+.

Workup

  1. customconsumption of starting material
  2. additiondiluted with Et2O
  3. filtrationThe precipitate is filtered
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-6457eadb02f34630b5587e41fbdadc41
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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