Potassium Hydroxide → HCID 59589749, compound

HRID 1054394Notes

Reaction equation

HRID 1054394 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:23][CH:22]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:6]=1)C.[OH-].[K+]>C(O)C>[N:30]1([CH2:29][CH2:28][O:27][C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:18]3[N:19]=[C:15]4[CH:14]=[CH:13][CH:12]=[C:11]([C:7]5[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=5)[C:4]([OH:35])=[O:3])[N:16]4[N:17]=3)=[CH:22][CH:23]=2)[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59589941HCID 59589941, compound

Product 1

HCID 59589749HCID 59589749, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzoic acid ethyl ester (1.28 g, 2.71 mmol) was dissolved in ethanol (20 ml) and potassium hydroxide (0.45 g, 8.12 mmol) was added. The reaction was heated to reflux for 3 hrs. Upon cooling the solvent was removed in vacuo and aqueous sodium hydrogencarbonate added to the residue. The basic aqueous layer was washed with dichloromethane, then neutralised with 2M HCl and the resulting precipitate collected by filtration, washed with water and toluene, then dried under vacuum to give the desired product. Yield: 0.64 g, 53%. LCMS RT: 2.45 min, MI: 444, Method: 2.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hrs
  3. temperatureUpon cooling the solvent
  4. customwas removed in vacuo and aqueous sodium hydrogencarbonate
  5. additionadded to the residue
  6. washThe basic aqueous layer was washed with dichloromethane
  7. filtrationthe resulting precipitate collected by filtration
  8. washwashed with water and toluene
  9. customdried under vacuum

Sources & evidence

ORD record
ord-50e97e977bfd4d0d984c59d3d945386f
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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