Hydrochloric Acid → HCID 22485022, compound

HRID 1368252Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]2[C:25]3=[N:26][C:27]([C:30]([O:32]C)=[O:31])=[CH:28][CH:29]=[C:24]3[N:23]=[C:22]2[CH3:34])=[C:18]([Cl:37])[CH:17]=1)C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C:16]1[CH:36]=[CH:35][C:19]([CH2:20][N:21]2[C:25]3=[N:26][C:27]([C:30]([OH:32])=[O:31])=[CH:28][CH:29]=[C:24]3[N:23]=[C:22]2[CH3:34])=[C:18]([Cl:37])[CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3-(4-(N,N-bis-(tert-butoxycarbonyl)amino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (391 mg) was dissolved in 1,4-dioxane (4 ml). 1N Aqueous sodium hydroxide solution (3.7 ml) was added and the mixture was stirred at room temperature for 2 days and at 80° C. for 2 hr. To the reaction mixture was added 1N hydrochloric acid to adjust the pH to 4. Water (40 ml) was added and the precipitated crystals were collected by filtration to give 3-(4-(N-(tert-butoxycarbonyl)-amino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (261 mg) as pale-yellow crystals.

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-b1a7fd0d577e470a8c6b51b4c909d1ec
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573274B1

Reaction notes

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