Water → HCID 178517324, compound

HRID 388599Notes

Reaction equation

HRID 388599 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][CH2:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[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]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86633720HCID 86633720, compound

Product 1

HCID 178517324HCID 178517324, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

THF (50 mL) and 1,1′-carbonyldiimidazole (4.2 g, 26 mmol) were sequentially added to a solution of 2-chloro-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (5 g, 17 mmol) in pyridine (50 mL), and the reaction was heated at 90° C. overnight. The reaction was cooled to approximately 0° C., and water (400 mL) was added. The mixture was stirred for 30 minutes. A precipitate was present and was isolated by filtration and washed with water and diethyl ether to provide 4 g of 4-chloro-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol. A small portion of the product was triturated with hot acetonitrile, isolated by filtration, and washed with cold acetonitrile and diethyl ether to provide beige needles with the following analytical data, mp greater than 275° C.

Workup

  1. temperatureThe reaction was cooled to approximately 0° C.
  2. customwas isolated by filtration
  3. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-c77bc4cbeafc4b7ebfc3abbffe7933b5
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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