Trifluoroacetic acid → HCID 178433876, compound

HRID 1445321Notes

Reaction equation

HRID 1445321 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:34])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[NH:33][N:32]=[N:31][N:30]=5)[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:35])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[OH:37][CH2:38][CH2:39][N+:40]([CH3:43])([CH3:42])[CH3:41].FC(F)(F)C(O)=O>C(O)C.O.CO>[OH:37][CH2:38][CH2:39][N+:40]([CH3:43])([CH3:42])[CH3:41].[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:34])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[NH:30][N:31]=[N:32][N:33]=5)[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:35])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31255Choline, hydroxideHCID 178433875HCID 178433875, compound

Product 1

HCID 178433876HCID 178433876, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
78 °C

Procedure

2-(3,4-Dimethylphenyl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one (2.0 g, 4.29 mmole) was suspended in ethanol (17 ml) and water (1.85 ml). The brown slurry was treated with choline hydroxide (2.68 ml, 2.2 eq) (supplied as a 45% wt solution in methanol) at ambient temperature to form a deep purple solution which was stirred for 30 mins. The solution was filtered, and rinsed through with ethanol (4 ml). Triflouroacetic acid (0.36 ml, 1 eq) in water (1.85 ml) was added to the filtrate to form an orange-red slurry which was then heated to 78° C. (reflux) and stirred for 30 mins. The reaction was then cooled to 60° C. and treated with ethanol (25 ml, 12.5 vol) and stirred for a further 1 h at 60° C. The suspension was then cooled to ambient and stirred for 17 h. After filtration the cake was washed with ethanol (8 ml, 4 vol). The resulting solid was dried at 50° C. in vacuo to give 2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline as an orange solid (2.02 g, 83%).

Workup

  1. customat ambient temperature
  2. customto form a deep purple solution which
  3. filtrationThe solution was filtered
  4. washrinsed through with ethanol (4 ml)
  5. customto form an orange-red slurry which
  6. temperature(reflux)
  7. stirringstirred for 30 mins
  8. temperatureThe reaction was then cooled to 60° C.
  9. stirringstirred for a further 1 h at 60° C
  10. temperatureThe suspension was then cooled to ambient and
  11. stirringstirred for 17 h
  12. filtrationAfter filtration the cake
  13. washwas washed with ethanol (8 ml, 4 vol)
  14. customThe resulting solid was dried at 50° C. in vacuo

Sources & evidence

ORD record
ord-9ea8650bc3aa4c039fb012b8533e9fa4
Source dataset
uspto-grants-2010_02
Patent number
US07666857B2

Reaction notes

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