HCID 58081337, compound → HCID 58081240, compound

HRID 928376Notes

Reaction equation

HRID 928376 reaction equation
[N:1]1([CH2:6][C:7]2[CH:23]=[CH:22][C:10]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:14]=[N:13]3)=[CH:9][C:8]=2[O:24][CH3:25])[CH:5]=[CH:4][CH:3]=[N:2]1>C1COCC1.CCO.O>[N:1]1([CH2:6][C:7]2[CH:23]=[CH:22][C:10]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[N:13]3)=[CH:9][C:8]=2[O:24][CH3:25])[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

3

Reactant 1

HCID 58081337HCID 58081337, compound

Product 1

HCID 58081240HCID 58081240, compound

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of crude ethyl 1-(4-((1H-pyrazol-1-yl)methyl)-3-methoxybenzyl)-1H-pyrazole-4-carboxylate (998 mg, 29%, 0.85 mmol) in THF:EtOH:H2O 2:1:1 (15 ml), LiOH Monohydrate (107 mg, 2.55 mmol) was added and stirred for 12 h at 50° C. The reaction mixture was concentrated under reduced pressure. The remaining solid was taken up in ethyl acetate and extracted with water. The aqueous phase was acidified by adding aqueous HCl and extracted with ethy acetate. The organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude 1-(4-((1H-pyrazol-1-yl)methyl)-3-methoxybenzyl)-1H-pyrazole-4-carboxylic acid. MS [M+H]+=313.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with water
  3. additionby adding aqueous HCl
  4. extractionextracted with ethy acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08e5c856262b47da98bdc189d439abcd
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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