Water → HCID 178461675, compound

HRID 388592Notes

Reaction equation

C1C[O:4][CH2:3]C1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:18][C:19]1[C:28]([NH2:29])=[C:27]([NH:30][C@@H:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH3:32])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.O>N1C=CC=CC=1>[Cl:18][C:19]1[C:28]2[N:29]=[C:3]([OH:4])[N:30]([C@@H:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:32])[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

THF (100 mL) and 1,1′-carbonyldiimidazole (8.1 g, 50.5 mmol) were sequentially added to a solution of 2-chloro-N4-[(1R)-1-phenylethyl]quinoline-3,4-diamine (10.0 g, 33.6 mmol) in pyridine (100 mL), and the reaction was heated at 90° C. overnight. An analysis by LC/MS indicated the presence of starting material, and additional 1,1′-carbonyldiimidazole (6 equivalents) was added in portions as heating at 90° C. was continued for a second day. The reaction was cooled to approximately 0° C., and water (300 mL) was added. The mixture was stirred overnight. A precipitate was present and was isolated by filtration and washed with water and diethyl ether to provide 6.67 g of 4-chloro-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol. A small portion of the product was triturated with hot acetonitrile, isolated by filtration, washed with cold acetonitrile and diethyl ether, and dried under vacuum to provide a white solid with the following analytical data, mp 227-229° C.

Workup

additionwas added in portions
temperatureas heating at 90° C.
waitwas continued for a second day
temperatureThe reaction was cooled to approximately 0° C.
customwas isolated by filtration
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-0e08bb6bdf81478096d5b14acf6aef34
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377957B2

Reaction notes

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