Hydrochloric Acid → HCID 18975307, compound

HRID 2393450Notes

Reaction equation

HRID 2393450 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:14]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:13][NH:12][C:9]3=[CH:10][N:11]=2)[CH:5]=1.[OH-].[Na+].Cl>CO>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:14]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][NH:12][C:9]3=[CH:10][N:11]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18975318HCID 18975318, compound

Product 1

HCID 18975307HCID 18975307, compoundYield 223.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 3-(5-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionate (0.115 g, 0.4 mmol) in methanol (5 mL) was added NaOH (4M, 0.5 mL, 2 mmol) and the mixture heated at 40° C. for 16 hours. After cooling the solution was neutralised (5M HCl) and the solvents evaporated to give 3-(5-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.23 g) as a colourless solid. 1H NMR (360 MHz, d6 -DMSO) δ 2.48-2.55 (2H, m), 2.96 (2H, t, J=7.1Hz), 7.54 (1H, s), 8.03 (1H, s), 8.62 (1H, s), 9.24 (2H, s) and 11.81 (1H, br s). This was used without further purification in the next step.

Workup

  1. temperatureAfter cooling the solution
  2. customthe solvents evaporated

Sources & evidence

ORD record
ord-8b64d5342f7d4fa0be910c7f07ddfdeb
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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