Water → HCID 178525476, compound

HRID 388610Notes

Reaction equation

HRID 388610 reaction equation
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[NH2:13][C:14]1[C:15]([Cl:29])=[N:16][C:17]2[C:22]([C:23]=1[NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:21][CH:20]=[CH:19][CH:18]=2.N1C=CC=CC=1.O.C1C[O:40][CH2:39]C1>>[N:3]1([C:1]([O:28][CH2:27][CH2:26][CH2:25][N:24]2[C:23]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]=[C:15]([Cl:29])[C:14]=3[N:13]=[C:39]2[OH:40])=[O:2])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole2×HCID 866337283-[(3-Amino-2-chloroquinolin-4-yl)amino]propan-1-ol

Product 1

HCID 178525476HCID 178525476, compound

Procedure

1,1′-Carbonyldiimidazole (25 g, 155 mmol) was added to a solution of 3-[(3-amino-2-chloroquinolin-4-yl)amino]propan-1-ol (26 g, 0.010 mol) in THF (140 mL), and the reaction was stirred for three hours at room temperature. Additional 1,1′-carbonyldiimidazole (25 g) and pyridine (50 mL) were added, and the reaction was heated at 90° C. for three hours and allowed to cool. The reaction was cooled to 0° C., and water (300 mL) was added. The resulting mixture was stirred for 30 minutes, and a precipitate formed. The precipitate was isolated by filtration and washed with water to provide 38 g of 3-(4-chloro-2-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)propyl 1H-imidazole-1-carboxylate as a white solid.

Workup

  1. temperaturethe reaction was heated at 90° C. for three hours
  2. temperatureto cool
  3. temperatureThe reaction was cooled to 0° C.
  4. stirringThe resulting mixture was stirred for 30 minutes
  5. customa precipitate formed
  6. customThe precipitate was isolated by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-39d40d454cda4958b964d6ca90a2e815
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

Loading…