Hydrochloric Acid → HCID 178453117, compound

HRID 908248Notes

Reaction equation

HRID 908248 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[NH:22][C:13]2=[N:14][CH:15]=[C:16]([C:18]([O:20]C)=[O:19])[CH:17]=[C:12]2[N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[NH:22][C:13]2=[N:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[CH:17]=[C:12]2[N:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178498759HCID 178498759, compound

Product 1

HCID 178453117HCID 178453117, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a MeOH—H2O (5:1) 72 mL solution of methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-3H-imidazo[4,5-b]pyridine-6-carboxylate (11.0 g, 37.6 mmol) was added lithium hydroxide monohydrate (7.5 g, 179 mmol). After stirring at 60° C. for 4 hr, the reaction mixture was cooled to 0 acidified by 1N HCl to pH 5, concentrated and purified by Prep-HPLC (77×250 mm, JT BAKER C-18 RP column, 10μ particle size, linear gradient, 5% MeCN/H2O+0.1% TFA to 35% MeCN/H2O+0.1% TFA@200 mL/min) to give the title compound (7.5 g, 71%). MS (ESI): m/z 293(M+H). 1H-NMR (400 MHz, d6-DMSO): δ 13.04 (br. s, 1H), 8.84 (s, 1H), 8.31 (s, 1H), 7.56 (s, 1H), 4.39 (s, 2H), 1.35 (s, 9H).

Workup

  1. temperaturethe reaction mixture was cooled to 0
  2. concentrationconcentrated
  3. custompurified by Prep-HPLC (77×250 mm, JT BAKER C-18 RP column, 10μ particle size, linear gradient, 5% MeCN/H2O+0.1% TFA to 35% MeCN/H2O+0.1% TFA@200 mL/min)

Sources & evidence

ORD record
ord-22b95566f14d442aaedd6db57ec8e77a
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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