Hydrochloric Acid → 2-(4-Carboxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline

HRID 1384918Notes

Reaction equation

HRID 1384918 reaction equation
O1CCCC1.[OH-].[Na+].C([O:10][C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([Cl:39])[CH:32]=3)[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:40]#[N:41])[CH:25]=3)[N:20]=2)[CH2:15][CH2:14]1)=[O:12])C.Cl>O.C(O)C>[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([Cl:39])[CH:32]=3)[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:40]#[N:41])[CH:25]=3)[N:20]=2)[CH2:15][CH2:14]1)([OH:12])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 211839262-(4-Ethoxycarbonylpiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline

Product 1

HCID 211838902-(4-Carboxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazolineYield 91.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

30 ml of tetrahydrofuran, 30 ml of ethanol and 14 ml of a 1N aqueous solution of sodium hydroxide were added to 1.0 g of 2-(4-ethoxycarbonylpiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinazoline. The obtained mixture was stirred at room temperature for 16 hours and neutralized with 1 N hydrochloric acid, followed by the addition of 100 ml of water. The crystals thus precipitated were recovered by filtration and recrystallized from tetrahydrofuran/ethanol/water to give 860 mg of the title compound.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere recovered by filtration
  3. customrecrystallized from tetrahydrofuran/ethanol/water

Sources & evidence

ORD record
ord-549da04f36254f59bee8d646a5979780
Source dataset
uspto-grants-2001_07
Patent number
US06262059B1

Reaction notes

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