Phenyl isocyanate → HCID 10115890, compound

HRID 431469Notes

Reaction equation

HRID 431469 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][CH3:25])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][N:24]([CH3:25])[C:33]([NH:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:34])[C:7]=2[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 18761297HCID 18761297, compound

Product 1

HCID 10115890HCID 10115890, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Methoxyethyl)-1-{2-[2-(methylamino)ethoxy]ethyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-4-amine (750 mg, 2.16 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and treated with phenyl isocyanate (239 μL, 2.20 mmol). After stirring under N2 overnight, the reaction mixture was concentrated under reduced pressure. Crystallization from EtOAc and CH2Cl2 gave 170 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy} ethyl)-N-methyl-N′-phenylurea as fluffy white crystals. m.p. 167.7-170.0° C.;

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customCrystallization from EtOAc and CH2Cl2

Sources & evidence

ORD record
ord-517f3919cafe4f15b1e6e1369e761978
Source dataset
uspto-grants-2003_12
Patent number
US06660735B2

Reaction notes

Loading…