Ammonia → 2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606037Notes

Reaction equation

HRID 606037 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:27][O:28][CH2:29][CH3:30])[N:14]([CH2:15][CH:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:31].C(Cl)(Cl)Cl.ClCCl>CO>[CH2:29]([O:28][CH2:27][C:13]1[N:14]([CH2:15][CH:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17]2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:31])[C:11]=2[N:12]=1)[CH3:30]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 6344DichloromethaneHCID 866168714-chloro-2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 590267062-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (1.50 g, 3.56 mmol) was treated with a solution of 7 M ammonia in methanol (30 mL) at 140° C. for 15 hours according to the method described in Part F of Example 1. Chloroform was used in the work-up procedure instead of dichloromethane. The crude product was purified by flash chromatography (silica gel, elution with 97:3 dichloromethane/methanol) to afford 2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.17 g) as a yellow solid. Recrystallization afforded white needles, mp 235-237° C.

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, elution with 97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-d5258e7d6a514aa9aac2562f51c8eb11
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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