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

HRID 2392899Notes

Reaction equation

HRID 2392899 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 1N 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-fe521ccf188a45978c7c83efbf0d6ff2
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

Loading…