Hydrochloric Acid → HCID 178439663, compound

HRID 1194688Notes

Reaction equation

HRID 1194688 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([CH2:21][CH2:22][C:23]#[N:24])[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].Cl>O1CCCC1>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[C:15]3=[N:16][CH:17]=[C:18]([CH2:21][CH2:22][C:23]4[NH:33][N:32]=[N:31][N:24]=4)[C:19](=[O:20])[N:14]3[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 14130383HCID 14130383, compound

Product 1

HCID 178439663HCID 178439663, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.07 g (2.65 mmoles) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl ]-3-(2-cyanoethyl)-4H-pyrido[1,2-a]pyrimidin-4-one, 1.76 g 2.57 g (39.53 mmoles) of sodium azide and 45 ml of tetrahydrofuran was heated under reflux for 23 hours. After cooling, the resulting reaction solution was poured into ice water and then acidified with dilute hydrochloric acid. The precipitate so formed was separated by filtration and recrystallized from acetonitrile to obtain 0.70 g (59% yield) of 9-[(4-acetyl-3-hydroxy-2-n-propylphenoxy)methyl]-3-[2-(1H-tetrazol-5-yl)ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one in the form of white crystals. These crystals had a melting point of 238°-239° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 23 hours
  3. temperatureAfter cooling
  4. customthe resulting reaction solution
  5. customThe precipitate so formed
  6. customwas separated by filtration
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c2156260763349c9b3e970b0383efbec
Source dataset
uspto-grants-1989_03
Patent number
US04816459

Reaction notes

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