Sodium hydride → 1-(2-{(1S,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}ethyl)-3-methylimidazolidine-2,4-dione

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	2,4-Imidazolidinedione, 3-methyl-	HCID 138851	—
Reactant	1-(2,2-Dimethylpropyl)-3-methyl-5-{(1R,25)-2-[2-(methylsulfonyl)ethyl]-cyclopropyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one	HCID 117702368	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(2-{(1S,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}ethyl)-3-methylimidazolidine-2,4-dione	HCID 117702490	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

1-(2,2-Dimethylpropyl)-3-methyl-5-{(1R,2S)-2-[2-(methylsulfonyl)ethyl]-cyclopropyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (32-5, 39 mg, 0.10 mmol, 1.0 equiv) was added to anhydrous DMF (0.50 mL) and cooled to 0° C. 3-Methylimidazolidine-2,4-dione (31-6, 58 mg, 0.51 mmol, 5.0 equiv) and NaH (20 mg, 0.51 mmol, 5.0 equiv, 60% dispersion in oil) were added sequentially and the resulting mixture was warmed to RT. After 18 h, LCMS showed complete consumption of 32-5. Purification by reverse-phase HPLC (10-100% 0.1% TFA in H2O:CH3CN) afforded 32-6 as a colorless oil. MS m/z (M+H): calculated=400.2343; observed=400.2342.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315518B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-80ef589b16d1412e807a75247afbdf79
Source note	uspto-grants-2016_04