2-Imidazolidinone → HCID 90427256, compound

HRID 2278995Notes

Reaction equation

HRID 2278995 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].[CH3:19][N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([O:31][C:32]3[CH:33]=[CH:34][C:35]([NH2:38])=[N:36][CH:37]=3)[CH:28]=[CH:27][N:26]=2)[CH:22]=[N:21]1>CC#N>[CH3:19][N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[C:29]([O:31][C:32]3[CH:33]=[CH:34][C:35]([NH:38][C:2]([N:13]4[CH2:17][CH2:16][NH:15][C:14]4=[O:18])=[O:4])=[N:36][CH:37]=3)[CH:28]=[CH:27][N:26]=2)[CH:22]=[N:21]1

Participants

5

Reactant 3

HCID 84532-ImidazolidinoneHCID 94429TriphosgeneHCID 593227775-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-2-amine

Product 1

HCID 90427256HCID 90427256, compoundYield 134.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

A 0° C. solution of triphosgene (0.500 g, 1.685 mmol) in MeCN (10 mL) was treated with a solution of imidazolidin-2-one (0.800 g, 9.29 mmol) in MeCN (10 mL), stirred at RT for 0.5 h, added to a suspension of Example A2 (0.800 g, 2.99 mmol) in MeCN (10 mL) and stirred at RT for 4 h. The solids were collected via filtration to afford N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (862 mg, 76%) as an off-white solid. MS (ESI) m/z: 380.1 (M+H+).

Workup

  1. stirringstirred at RT for 4 h
  2. filtrationThe solids were collected via filtration

Sources & evidence

ORD record
ord-faff046e0abb4ae4bd01602eebdc4feb
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

Loading…