Ammonia → 2-(ethoxymethyl)-1-[2-(3-methyl-1-oxa-2,4-diazaspiro[4,4]non-2-en-4-yl)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606085Notes

Reaction equation

HRID 606085 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][CH2:16][N:17]3[C:21]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[O:20][N:19]=[C:18]3[CH3:26])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:31]>CO>[CH2:29]([O:28][CH2:27][C:13]1[N:14]([CH2:15][CH2:16][N:17]2[C:21]3([CH2:25][CH2:24][CH2:23][CH2:22]3)[O:20][N:19]=[C:18]2[CH3:26])[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

4

Reactant 2

HCID 222AmmoniaHCID 866168874-chloro-2-(ethoxymethyl)-1-[2-(3-methyl-1-oxa-2,4-diazaspiro[4,4]non-2-en-4-yl)ethyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 590266802-(ethoxymethyl)-1-[2-(3-methyl-1-oxa-2,4-diazaspiro[4,4]non-2-en-4-yl)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methods described in Part H of Example 10 were used to treat 4-chloro-2-(ethoxymethyl)-1-[2-(3-methyl-1-oxa-2,4-diazaspiro[4,4]non-2-en-4-yl)ethyl]-1H-imidazo[4,5-c]quinoline (770 mg, 1.80 mmol) with a solution of 7 M ammonia in methanol (20 mL) and isolate and purify the final product to provide 700 mg of 2-(ethoxymethyl)-1-[2-(3-methyl-1-oxa-2,4-diazaspiro[4,4]non-2-en-4-yl)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine as white needles, mp 211-213° C.

Workup

  1. customisolate
  2. custompurify the final product

Sources & evidence

ORD record
ord-49c751bc0cf145c79de115551c6e10e0
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

Loading…