Hydrochloric Acid → HCID 178439661, compound

HRID 1194686Notes

Reaction equation

HRID 1194686 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([CH2:21][C:22]#[N:23])[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:26][CH2:27][CH3:28])[C:5]=1[OH:29])(=[O:3])[CH3:2].[Cl-].[NH4+].[N-:32]=[N+:33]=[N-:34].[Na+].Cl>CN(C)C=O>[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([CH2:21][C:22]4[NH:34][N:33]=[N:32][N:23]=4)[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:26][CH2:27][CH3:28])[C:5]=1[OH:29])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14130382HCID 14130382, compound

Product 1

HCID 178439661HCID 178439661, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 recrystallized from dimethylformamide to obtain 0.55 g (48% 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 pale-yellow crystals. These crystals had a melting point of 250°-253° C. (dec.).

Workup

  1. temperaturewas heated at 100°-110° C. for 8 hours
  2. temperatureAfter cooling
  3. customthe resulting reaction solution
  4. customThe precipitate so formed
  5. filtrationwas collected by filtration
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-914538067e0a4919a0f51ca6768fde05
Source dataset
uspto-grants-1989_03
Patent number
US04816459

Reaction notes

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