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

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	2,4-Imidazolidinedione, 3-methyl-	HCID 138851	—
Reactant	{(1R,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}methyl methanesulfonate	HCID 117702620	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-({(1R,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}methyl)-3-methylimidazolidine-2,4-dione	HCID 117702410	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

{(1R,2R)-2-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropyl}methyl methanesulfonate (31-5, 68 mg, 0.18 mmol, 1.0 equiv) was added to anhydrous DMF (0.92 mL) and cooled to 0° C. 3-Methylimidazolidine-2,4-dione (31-6, 105 mg, 0.92 mmol, 5.0 equiv) and NaH (37 mg, 0.92 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 31-5. Purification by reverse-phase HPLC (10-100% 0.1% TFA in H2O:CH3CN) afforded 31-7 as a colorless oil. MS m/z (M+H): calculated=332.1969; observed=332.1971.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315518B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-54806d4372ee41c192abfc246d989912
Source note	uspto-grants-2016_04