(4-Aminophenoxy)benzene → 3-[2-(4-Morpholinyl)ethyl]-8-(4-phenoxyanilino)-3H-imidazo[4,5-g]quinoline-7-carbonitrile

HRID 2213752Notes

Reaction equation

HRID 2213752 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:23]#[N:24].[O:25]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[N:17]1([CH2:16][CH2:15][N:14]2[C:8]3[C:9](=[CH:10][C:11]4[C:2]([NH:36][C:35]5[CH:34]=[CH:33][C:32]([O:25][C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=6)=[CH:38][CH:37]=5)=[C:3]([C:23]#[N:24])[CH:4]=[N:5][C:6]=4[CH:7]=3)[N:12]=[CH:13]2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 10176127Pyridinium chlorideHCID 219564158-chloro-3-[2-(4-morpholinyl)ethyl]-3H-imidazo[4,5-g]quinoline-7-carbonitrile

Product 1

HCID 103000663-[2-(4-Morpholinyl)ethyl]-8-(4-phenoxyanilino)-3H-imidazo[4,5-g]quinoline-7-carbonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 7, a mixture of 82.2 mg (0.24 mmol) of 8-chloro-3-[2-(4-morpholinyl)ethyl]-3H-imidazo[4,5-g]quinoline-7-carbonitrile, 53.3 mg (0.29 mmol) of 4-phenoxyaniline and 33.5 mg (0.29 mmol) of pyridine hydrochloride in 3.5 mL of 2-ethoxyethanol is heated at 130–135° C. for 1 hour to yield 81.2 mg (69%) of the product as a yellow solid, mp>260° C.

Workup

  1. temperatureis heated at 130–135° C. for 1 hour

Sources & evidence

ORD record
ord-8d75bae7a44941808a5b2a5d4919f9a7
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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