2-(ethoxymethyl)-7-(2-morpholin-4-ylethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 2-(ethoxymethyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 540953Notes

Reaction equation

HRID 540953 reaction equation
NC1C2N=C(C[O:19]CC)N(CCC)C=2C2C=CC(O)=CC=2N=1.[CH2:23]([O:25][CH2:26][C:27]1[N:28]([CH2:50][CH2:51][CH3:52])[C:29]2[C:38]3[CH:37]=[CH:36][C:35]([O:39][CH2:40][CH2:41][N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:34][C:33]=3[N:32]=[C:31]([NH2:48])[C:30]=2[N:49]=1)[CH3:24]>O>[CH2:23]([O:25][CH2:26][C:27]1[N:28]([CH2:50][CH2:51][CH3:52])[C:29]2[C:38]3[CH:37]=[CH:36][C:35]([O:39][CH2:40][C:41]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[O:19])=[CH:34][C:33]=3[N:32]=[C:31]([NH2:48])[C:30]=2[N:49]=1)[CH3:24]

Participants

4

Reactant 2

HCID 588337092-(ethoxymethyl)-7-(2-morpholin-4-ylethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 1360752014-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 588336272-(ethoxymethyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A modification on the procedure described in Example 646 was used to convert 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol (prepared as described in Parts A and B of Example 51) into 2-(ethoxymethyl)-7-(2-morpholin-4-ylethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine. The reaction mixture was heated overnight then was poured slowly into water. After the mixture was stirred for 1 hour, a tan solid was isolated by filtration and recrystallized from acetonitrile to afford 2-(ethoxymethyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as off-white crystals, mp 213° C.

Workup

  1. temperatureThe reaction mixture was heated overnight
  2. customa tan solid was isolated by filtration
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-dec1168d445c441a8a2c8c5ceb21b6ee
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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