Hydrochloric Acid → 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 1821810Notes

Reaction equation

HRID 1821810 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:23]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[NH:15][C:14]=12)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68982508HCID 68982508, compound

Product 1

HCID 689809557-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (Reference Example 3) (500 mg, 1.30 mmol), 2 M sodium hydroxide solution (6 mL), tetrahydrofuran (3 mL) and ethanol (3 mL) was refluxed for 2 h. The mixture was neutralized by addition of 1 M hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was crystallized from ethyl acetate to give 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (100 mg, 22%) as pale brown amorphous solid. Additional material (348 mg, 75%; 97% overall yield) was obtained from the mother liquid: Rf 0.01 (silica gel, ethyl acetate); mp 114-120° C.; 1H NMR (300 MHz, DMSO-d6) δ4.82 (4H, br s), 7.18-7.35 (12H, m), 7.68 (1H, d, J=6.0 Hz); ESI MS m/z 358 [C22H19N3O2+H]+; HPLC (Method A) 98.8% (AUC), tR=17.7 min.

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-818cd2f4c05a42d2b9083897ced212be
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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