Hydrochloric Acid → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[2-(2-oxo-1-pyrrolidinyl)ethoxy]methyl]-

HRID 2377110Notes

Reaction equation

HRID 2377110 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([O:18]C)=[O:17])[CH:15]=[C:10]3[C:9]([CH2:20][O:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][C:25]3=[O:29])=[CH:8]2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([OH:18])=[O:17])[CH:15]=[C:10]3[C:9]([CH2:20][O:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][C:25]3=[O:29])=[CH:8]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 691986491h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[2-(2-oxo-1-pyrrolidinyl)ethoxy]methyl]-,methyl ester

Product 1

HCID 598558171h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[2-(2-oxo-1-pyrrolidinyl)ethoxy]methyl]-Yield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of methyl 1-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.915 g, 2.15 mmol) in methanol (25 mL) was added 3M LiOH(aq) (2.15 mL, 6.45 mmol). The clear reaction was warmed to 50° C. for 16 hours. After 16 hours a 50° C. the reaction was acidified to pH 4 by the addition of 1M HCl(aq). The solvent was evaporated in vacuo and the white residue stirred in water (50 mL) for 1 hour. The solid was filtered, washed with water, and dried under heat and vacuum to yield 1-(4-fluorobenzyl)-3-{[2-(2oxopyrrolidin-1-yl)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid as a white solid (0.829 g, 94% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.76-1.85 (m, 2H) 2.13 (t, J=8.08 Hz, 2H) 3.31 (ddd, J=13.77, 6.69, 6.32 Hz, 4H) 3.52 (t, J=5.43 Hz, 2H) 4.66 (s, 2H) 5.57 (s, 2H) 7.16 (t, J=8.84 Hz, 2H) 7.35 (dd, J=8.46, 5.68 Hz, 2H) 7.86 (s, 1H) 8.33 (s, 1H) 8.95 (s, 1H).

Workup

  1. customThe clear reaction
  2. customThe solvent was evaporated in vacuo
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. temperatureunder heat

Sources & evidence

ORD record
ord-44056a8a7a5b4eb3b27cafc0886cda6f
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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