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 1399793Notes

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]

Participants

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

temperatureIt was cooled to room temperature
filtrationthe precipitate was collected by filtration
additionIt was then poured into water (100 mL)
filtrationIt was filtered
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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