Hydrochloric Acid → HCID 57310684, compound

HRID 2393438Notes

Reaction equation

HRID 2393438 reaction equation
[N:1]1([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]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].Cl>CO>[N:1]1([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]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18975315HCID 18975315, compound

Product 1

HCID 57310684HCID 57310684, compoundYield 168.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-(5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionate (0.43 g, 1.5 mmol) in methanol (20 mL) was added NaOH (4M, 1 mL) and the mixture was heated at 50° C. for 5 hours. After cooling the solution was neutralised (5M, HCl) and the solvents evaporated in vacuo to give 3-(5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.65 g) as a colourless solid. 1H NMR (360 MHz, d6 -DMSO) δ 2.60 (2H, t, J=7.5Hz), 2.98 (2H, t, J=7.4Hz), 7.55 (1H, s), 7.98 (1H, s), 8.23 (1H, s), 8.62 (1H, s), 9.24 (1H, s) and 11.74 (1H, br s). This was used without purification in the next step.

Workup

  1. temperatureAfter cooling the solution
  2. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-07483cec4cc6440b9c86c01ff8c000c3
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…