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

HRID 1399793
Notes
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Reaction equation

HRID 1399793 reaction equation
[Cl:1][C:2]1[C:3]([CH3:29])=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:10]2=[N:11][C:12]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:13][C:14]([C:15]([O:17]C)=[O:16])=[C:9]2[N:8]=[C:7]1[CH3:25]>[Li+].[OH-].C1COCC1>[Cl:1][C:2]1[C:3]([CH3:29])=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:10]2=[N:11][C:12]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[C:9]2[N:8]=[C:7]1[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 89647844methyl 3-(3-chloro-2-methylbenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Product 1

HCID 715832203-(3-chloro-2-methylbenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acidYield 71%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-(3-chloro-2-methylbenzyl)-2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (239 mg, 0.58 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 (100 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 (163 mg, 71%). LC/MS: MS (ES+) m/e 401 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 2.44 (s, 3H), 3.41 (s, 4H), 3.69 (s, 4H), 5.44 (s, 2H), 6.40 (d, J=7.5 Hz, 1H), 7.05-7.11 (m, 2H), 7.35 (d, 1H).

Workup

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (100 mL)
  4. filtrationIt was filtered
  5. washthe solid was washed with water

Sources & evidence

ORD record
ord-733a1048f11644b3a5d421fcba484725
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