HCID 19851953, compound → HCID 178439701, compound

HRID 1607152Notes

Reaction equation

HRID 1607152 reaction equation
[C:1]([C:4]1[CH:39]=[CH:38][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:14]([C:36]#[N:37])=[C:15]([NH:19][C:20]([C:22]3[N:26](CC4C=CC(OC)=CC=4)[N:25]=[N:24][N:23]=3)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH2:40][CH2:41][CH3:42])[C:5]=1[OH:43])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:1]([C:4]1[CH:39]=[CH:38][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:14]([C:36]#[N:37])=[C:15]([NH:19][C:20]([C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH2:40][CH2:41][CH3:42])[C:5]=1[OH:43])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19851953HCID 19851953, compound

Product 1

HCID 178439701HCID 178439701, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 7.05 g (12.06 mmol) of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-2-cyanophenyl}-1-(4-methoxybenzyl)-tetrazole-5-carboxamide in 150 ml of trifluoroacetic acid and 15 ml of anisole is heated under reflux for 30 minutes. The reaction mixture is concentrated under reduced pressure, approximately 200 ml of ether and 300 ml of petroleum ether are added and the crystals are filtered off. The resulting N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]- 2-cyanophenyl}-1H-tetrazole-5-carboxamide having a melting point of 206°-208° is dissolved in 50 ml of acetone while hot, and the calculated amount of triethanolamine in 30 ml of acetone is added thereto. After the addition of ether, crystallisation begins. The triethanolammonium salt of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-2-cyanophenyl}-1H-tetrazole-5-carboxamide having a melting point of 81° (decomposition) is obtained.

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure, approximately 200 ml of ether and 300 ml of petroleum ether
  3. additionare added
  4. filtrationthe crystals are filtered off
  5. dissolutionThe resulting N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]- 2-cyanophenyl}-1H-tetrazole-5-carboxamide having a melting point of 206°-208° is dissolved in 50 ml of acetone while hot, and the calculated amount of triethanolamine in 30 ml of acetone
  6. additionis added
  7. additionAfter the addition of ether, crystallisation

Sources & evidence

ORD record
ord-d58fa868ce00483d853424e7ede5012c
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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