Hydrochloric Acid → HCID 178439659, compound

HRID 1194685Notes

Reaction equation

HRID 1194685 reaction equation
[K].[C:2]([C:5]1[CH:28]=[CH:27][C:8]([O:9][CH2:10][C:11]2[C:16]3=[N:17][CH:18]=[C:19]([C:22]4[NH:26][N:25]=[N:24][N:23]=4)[C:20](=[O:21])[N:15]3[CH:14]=[CH:13][CH:12]=2)=[C:7]([CH2:29][CH2:30][CH3:31])[C:6]=1[OH:32])(=[O:4])[CH3:3].Cl>O>[C:2]([C:5]1[CH:28]=[CH:27][C:8]([O:9][CH2:10][C:11]2[C:16]3=[N:17][CH:18]=[C:19]([C:22]4[NH:26][N:25]=[N:24][N:23]=4)[C:20](=[O:21])[N:15]3[CH:14]=[CH:13][CH:12]=2)=[C:7]([CH2:29][CH2:30][CH3:31])[C:6]=1[OH:32])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178439660HCID 178439660, compound

Product 1

HCID 178439659HCID 178439659, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.00 g (2.65 mmoles) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-cyano-4H-pyrido[1,2-a]-pyrimidin-4-one, 0.97 g (7.27 mmoles) of aluminum chloride, 1.43 g (21.99 mmoles) of sodium azide and 20 ml of tetrahydrofuran was heated under reflux for 2 hours. After cooling, the resulting reaction solution was diluted with ice water and then acidified with dilute hydrochloric acid. The precipitate so formed was collected by filtration and dried. 1.09 g (2.59 mmoles) of this precipitate was suspended in 55 ml of menthanol and then dissolved therein by adding 3.00 ml (2.55 mmoles) of a 5.6% ethanolic solution of potassium hydroxide. The resulting solution was filtered to remove any insoluble matter, and the filtrate was cooled. The precipitate which separated out was collected by filtration to obtain 0.88 g (74% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-(1H- tetrazol-5-yl)-4H-pyrido[ 1,2-a]pyrimidin-4-one potassium salt. Subsequently, 0.88 g (1.92 mmoles) of this potassium salt was dissolved in 180 ml of water by warming and the resulting solution was neutralized with 1.23 ml (3.69 mmoles) of 3N hydrochloric acid. The precipitate so formed was collected by filtration to obtain 0.78 g (97% yield) of 9-[(4-acetyl-3- hydroxy-2-n-propylphenoxy)methyl]-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one in the form of a white powder. This powder had a melting point of 268°-271° C. (dec.) and its infrared absorption spectrum and elemental analysis were as follows:

Workup

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

Sources & evidence

ORD record
ord-090e840dbb824f48bc79c8dce83fd23d
Source dataset
uspto-grants-1989_03
Patent number
US04816459

Reaction notes

Loading…