Pyridine → HCID 178517323, compound

HRID 388585Notes

Reaction equation

HRID 388585 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[C:23]([NH2:24])=[C:22]([NH:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.N1C=CC=CC=1.C(OCC)C>C1COCC1>[Cl:13][C:14]1[C:23]2[N:24]=[C:1]([OH:2])[N:25]([CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 682631,1'-Carbonyldiimidazole3×HCID 86633712HCID 86633712, compound

Product 1

HCID 178517323HCID 178517323, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1,1′-Carbonyldiimidazole (3.20 g, 19.7 mmol) was added to 2-chloro-N4-(pyridin-3-ylmethyl)quinoline-3,4-diamine (5.09 g, 17.9 mmol) in THF (100 mL), and the resulting suspension was heated at 80° C. for three days. An analysis by LC/MS indicated the presence of starting material, and pyridine (100 mL) and additional 1,1′-carbonyldiimidazole (1 equivalent) were added. The reaction was stirred for two hours at 80° C., and additional 1,1′-carbonyldiimidazole (1 equivalent) was added. The reaction was stirred overnight at 80° C. and allowed to cool; a solid was present. Diethyl ether (50 mL) was added, and the solid was isolated by filtration and dried under vacuum to provide 4.2 g of 4-chloro-1-(pyridin-3-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol as a gray solid.

Workup

  1. additionwere added
  2. stirringThe reaction was stirred overnight at 80° C.
  3. temperatureto cool
  4. customthe solid was isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7a46bc9fbdff4022be427486a2cd9314
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

Loading…