Phenyl isocyanate → HCID 57545296, compound

HRID 2383109Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]2[C:17]3[CH:16]=[CH:15][C:14]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][C:12]=3[N:11]=[C:10]([NH2:26])[C:9]=2[N:27]=1.[C:37]1([N:43]=[C:44]=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>N1C=CC=CC=1>[NH2:26][C:10]1[C:9]2[N:27]=[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:44]([NH:43][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:45])[N:7]([CH2:28][CH2:29][O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:8]=2[C:17]2[CH:16]=[CH:15][C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:12]=2[N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2-(4-aminobutyl)-7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.40 g, 0.83 mmol) and pyridine (10 mL) was cooled to 0° C., and phenyl isocyanate (91 μL, 0.84 mmol) was added. The reaction was stirred for one hour and additional phenyl isocyanate (10 μL) was added. The reaction was stirred for one hour and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 95:5 chloroform:methanol), recrystallized from toluene, and dried in a vacuum oven to provide 150 mg of N-{4-[4-amino-7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}-N′-phenylurea as a white crystalline solid, mp 186.3-186.9° C.

Workup

stirringThe reaction was stirred for one hour
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluting with 95:5 chloroform:methanol)
customrecrystallized from toluene
customdried in a vacuum oven

Sources & evidence

ORD record: ord-c046460a024a44be900de3d16ed90e08
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263594B2

Reaction notes

Loading…