Sodium Hydroxide → HCID 67215464, compound

HRID 472926Notes

Reaction equation

[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:8]([C:10]1[N:14]2[CH:15]=[C:16]([C:19]([O:21]C)=[O:20])[CH:17]=[CH:18][C:13]2=[CH:12][N:11]=1)=[O:9]>O1CCOCC1.CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:8]([C:10]1[N:14]2[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:13]2=[CH:12][N:11]=1)=[O:9]

Participants

Conditions

Temperature: 60 °C

Procedure

1.64 ml (1.64 mmol) of a 1N aqueous sodium hydroxide solution are added to 530 mg (1.49 mmol) of methyl 3-(3-methoxy-4-nitrobenzoyl)imidazo[1,5-a]pyridine-6-carboxylate obtained in example 4 in a mixture of 20 ml of dioxane and 10 ml of methanol. The reaction medium is heated at 60° C. for 3 hours and then concentrated under reduced pressure. The residue is taken up in water and the aqueous phase obtained is washed with dichloromethane and then neutralized by addition of 1.64 ml of 1N hydrochloric acid. The precipitate formed is filtered off, washed with water and then dried. 405 mg of a yellow solid are collected. Melting point: 313° C.; 1H NMR (d6-DMSO): 4.01 (3H, s), 7.78 (1H, d), 7.98 (1H, s), 8.06-8.10 (3H, m), 8.15 (1H, s), 10.28 (1H, s)

Workup

concentrationconcentrated under reduced pressure
customthe aqueous phase obtained
washis washed with dichloromethane
additionneutralized by addition of 1.64 ml of 1N hydrochloric acid
customThe precipitate formed
filtrationis filtered off
washwashed with water
customdried
custom405 mg of a yellow solid are collected

Sources & evidence

ORD record: ord-ff55661534ae4933bdbefa8e822a92f8
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633216B2

Reaction notes

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