Diethyl Ether → [4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N'-phenylurea

HRID 1265050Notes

Reaction equation

HRID 1265050 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:23]2[C:22]([CH3:24])=[C:21]([CH3:25])[N:20]=[C:19]([NH2:26])[C:18]=2[N:17]=[C:16]1[CH2:27][CH2:28][CH2:29][CH3:30].C(OCC)C>ClCCl>[NH2:26][C:19]1[C:18]2[N:17]=[C:16]([CH2:27][CH2:28][CH2:29][CH3:30])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[C:23]=2[C:22]([CH3:24])=[C:21]([CH3:25])[N:20]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7672Phenyl isocyanateHCID 120210831-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10126861[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N'-phenylureaYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylisocyanate (0.056 mL, 0.5 mmol) was added to a chilled solution of of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The ice bath was removed. A white precipitate formed after 5 minutes. The reaction mixture was allowed to stir for 30 minutes and then it was concentrated under reduced pressure to provide an off-white crystalline solid. This material was isolated by filtration using a small amount of diethyl ether to transfer the material to the filter and then dried in an Abderhalden drying apparatus to provide 185 mg of N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N′-phenylurea, m.p. 195.8-196.8° C. Analysis: Calculated for C23H32N6O: %C, 67.62; %H, 7.89; %N, 20.57; Found: %C, 66.84; %H, 7.71; %N, 20.54.

Workup

  1. customThe ice bath was removed
  2. customA white precipitate formed after 5 minutes
  3. concentrationit was concentrated under reduced pressure
  4. customto provide an off-white crystalline solid
  5. customThis material was isolated by filtration
  6. filtrationfilter
  7. customdried in an Abderhalden
  8. customdrying apparatus

Sources & evidence

ORD record
ord-bd4537a02a02418ea1aa89c28a6bfc88
Source dataset
uspto-grants-2003_04
Patent number
US06545017B1

Reaction notes

Loading…