Sodium Bicarbonate → 2-[5-(Hydroxymethyl)pyridin-2-yl]-4-[4-(trifluoromethyl)-1H-imidazol-1-yl]-1,2-dihydro-3H-pyrazol-3-one

HRID 1753826Notes

Reaction equation

HRID 1753826 reaction equation
C(O[C:4](=[O:19])[C:5]([N:10]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[CH:11]1)=[CH:6][N:7](C)C)C.[NH:20]([C:22]1[N:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=1)N.C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[OH:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([N:20]2[C:4](=[O:19])[C:5]([N:10]3[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[N:12]=[CH:11]3)=[CH:6][NH:7]2)=[N:27][CH:26]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 59186956(6-Hydrazinopyridin-3-yl)methanol2×HCID 674569553-(Dimethylamino)-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]acrylic acid ethyl ester

Product 1

HCID 596035882-[5-(Hydroxymethyl)pyridin-2-yl]-4-[4-(trifluoromethyl)-1H-imidazol-1-yl]-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (3.6 mmol) of the compound from Example 44A and 502 mg (3.6 mmol) of the compound from Example 4A are dissolved in 1 ml glacial acetic acid and the mixture is stirred at RT for 16 h. Thereafter, 200 mg (1.4 mmol) of the compound from Example 4A are again added and the mixture is stirred at RT for a further 20 h. The reaction mixture is taken up in 5 ml ethyl acetate and the mixture is adjusted to pH 7 with dilute aqueous sodium bicarbonate solution. The aqueous phase is concentrated in vacuo, 1.5 ml (4.0 mmol) 21% strength ethanolic sodium ethylate solution are added to the residue and the mixture is stirred at RT for 4 h. The precipitate is filtered off and washed with ethanol.

Workup

  1. stirringthe mixture is stirred at RT for a further 20 h
  2. concentrationThe aqueous phase is concentrated in vacuo, 1.5 ml (4.0 mmol) 21% strength ethanolic sodium ethylate solution
  3. additionare added to the residue
  4. stirringthe mixture is stirred at RT for 4 h
  5. filtrationThe precipitate is filtered off
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-78959f3b50ff497297ba462f057e7f1b
Source dataset
uspto-grants-2015_10
Patent number
US09168249B2

Reaction notes

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