Triethylamine → 2-(4-Ethoxycarbonylpiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline

HRID 1900689Notes

Reaction equation

HRID 1900689 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:20]1[N:29]=[C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([Cl:40])[CH:33]=2)[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:41]#[N:42])[CH:26]=2)[N:21]=1>CC(O)C>[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([C:20]2[N:29]=[C:28]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([Cl:40])[CH:33]=3)[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:41]#[N:42])[CH:26]=3)[N:21]=2)[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 211840042-Chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline

Product 1

HCID 211839262-(4-Ethoxycarbonylpiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazolineYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.5 g of ethyl isonipecotate, 2.25 g of triethylamine and 30 ml of 2-propanol were added to 1 g of 2-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline. The obtained mixture was refluxed for 30 minutes and cooled to room temperature. The crystals thus precipitated were recovered by filtration and washed with water and ethanol successively to give 1.13 g of the title compound.

Workup

  1. temperatureThe obtained mixture was refluxed for 30 minutes
  2. customThe crystals thus precipitated
  3. filtrationwere recovered by filtration
  4. washwashed with water and ethanol successively

Sources & evidence

ORD record
ord-dac79d8ce2ae447fb16c2b824ce46a91
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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