Sodium hydride → HCID 59727072, compound

HRID 1363146Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([C@@H:19]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH3:20])[C:9](=[O:18])[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[CH:4][CH:3]=1.F[C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:31]#[N:32].[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[C:31]([C:30]1[CH:33]=[CH:34][C:35]([N+:36]([O-:38])=[O:37])=[C:28]([NH:1][C:2]2[N:7]=[C:6]3[N:8]([C@@H:19]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH3:20])[C:9](=[O:18])[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:5]3=[CH:4][CH:3]=2)[CH:29]=1)#[N:32]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of (R)-tert-butyl 5-amino-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (94 mg) and 3-fluoro-4-nitrobenzonitrile (225 mg) in DMF (6 mL) was cooled to −25° C. and treated with NaH (60% w/w in mineral oil, 75 mg) and slowly allowed to warm to −15° C. The mixture was stirred for four hours between −20° C. and −15° C., then diluted with EtOAc and quenched with saturated ammonium chloride solution. The organic phase was washed three times with brine, separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2% MeOH in methylene chloride) provided 100 mg (R)-tert-Butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (70).

Workup

customquenched with saturated ammonium chloride solution
washThe organic phase was washed three times with brine
customseparated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d329f9ffa4c14626ae173553d31a640f
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884109B2

Reaction notes

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