Hydrochloric Acid → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 1696223Notes

Reaction equation

HRID 1696223 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=[C:10]3[NH:19][CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]3[NH:19][CH:20]=[CH:21][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58382222HCID 58382222, compound

Product 1

HCID 672772414-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]-pyridine-5-carboxylate (7 mg) in ethanol was added 1M NaOH solution and the mixture was stirred at 90° C. for 18 hours The mixture was cooled to 4° C. and acidified with 1M HCl and extracted with a 4:1 solution of chloroform and methanol. The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure to give 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (6.3 mg) as a white solid.

Workup

  1. temperaturewas cooled to 4° C.
  2. extractionextracted with a 4:1 solution of chloroform and methanol
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6521f9eaf14349d0aedc3e18f2c01b89
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…