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methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399791
Notes
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Reaction equation

HRID 1399791 reaction equation
[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([O:16]C)=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]>[Li+].[OH-].C1COCC1>[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[C:8]2[N:7]=[C:6]1[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 89648260methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Product 1

HCID 716106943-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acidYield 63%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-(2,3-dichlorobenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (239 mg, 0.55 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 60° C. for 5 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was washed with water to afford the desired product as a gray solid (146 mg, 63%); LC/MS: MS (ES+) m/e 421 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.46 (s, 3H), 3.39 (t, J=4.8 Hz, 4H), 3.67 (t, J=4.8 Hz, 4H), 5.50 (s, 2H), 6.67 (d, J=4.5 Hz, 1H), 7.04 (s, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.60 (d, J=4.5 Hz, 1H), 8.14 (s, 1H).

Workup

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (50 mL)
  4. filtrationIt was filtered
  5. washthe solid was washed with water

Sources & evidence

ORD record
ord-4461bd9a640f485b870c29e1cba5f220
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906910B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes