Hydrochloric Acid → HCID 178439661, compound

HRID 1194687Notes

Reaction equation

HRID 1194687 reaction equation
[Na].[C:2]([C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][C:11]2[C:16]3=[N:17][CH:18]=[C:19]([CH2:22][C:23]4[NH:27][N:26]=[N:25][N:24]=4)[C:20](=[O:21])[N:15]3[CH:14]=[CH:13][CH:12]=2)=[C:7]([CH2:30][CH2:31][CH3:32])[C:6]=1[OH:33])(=[O:4])[CH3:3].Cl>O>[C:2]([C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][C:11]2[C:16]3=[N:17][CH:18]=[C:19]([CH2:22][C:23]4[NH:24][N:25]=[N:26][N:27]=4)[C:20](=[O:21])[N:15]3[CH:14]=[CH:13][CH:12]=2)=[C:7]([CH2:30][CH2:31][CH3:32])[C:6]=1[OH:33])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178439662HCID 178439662, compound

Product 1

HCID 178439661HCID 178439661, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.04 g (2.65 mmoles) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-cyanomethyl-4H-pyrido[1,2-a]pyrimidin- 4-one, 1.00 g (18.69 mmoles) of ammonium chloride, 1.21 g (18.61 mmoles) of sodium azide and 30 ml of dimethylformamide was heated at 100°-110° C. for 8 hours with stirring. After cooling, the resulting reaction solution was poured into ice water and then acidified with dilute hydrochloric acid. The precipitate so formed was collected by filtration and then dried. 1.10 g (2.53 mmoles) of this precipitate was suspended in 70 ml of methanol and dissolved therein by adding 2.30 ml (2.30 mmoles) of a 4.2% aqueous solution of sodium hydroxide. The resulting solution was filtered to remove any insoluble matter. The filtrate was evaporated to dryness under reduced pressure to obtain 1.05 g (91% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-[(1H-tetrazol-5-yl)methyl]-4H-pyrido[1,2-a]pyrimidin-4-one sodium salt. Subsequently, 1.05 g (2.30 mmoles) of this sodium salt was dissolved in 260 ml of water and the resulting solution was neutralized with 1.50 ml (4.50 mmoles) of 3N hydrochloric acid. The precipitate so formed was collected by filtration and then dried to obtain 0.97 g (97% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-[(1H-tetrazol-5-yl)methyl]-4H-pyrido[1,2-a]pyrimidin-4-one in the form of a pale-yellow powder. This pcwder had a melting point of 248°-253° C. (dec.) and its infrared absorption spectrum and elemental analysis were as follows:

Workup

  1. customThe precipitate so formed
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-d2bcca8726a24975b46d4b8ab7ecd882
Source dataset
uspto-grants-1989_03
Patent number
US04816459

Reaction notes

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