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

HRID 1942025
Notes
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Reaction equation

HRID 1942025 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 176
Acetic Acid
Solvent
HCID 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-6fd94a16f3fc4594b7daaac9e450cd02
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389520B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes