Sodium Hydroxide → HCID 67466725, compound

HRID 1506589Notes

Reaction equation

HRID 1506589 reaction equation
[OH-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:29])[CH2:18][N:19]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[N:20]3)[CH2:13][CH2:12]2)[S:9][CH:10]=1)(=[O:5])[CH3:4].[F:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:32]=1[CH:33]=O>CO.O>[F:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:32]=1/[CH:33]=[CH:4]/[C:3]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:29])[CH2:18][N:19]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:26])([F:28])[F:27])=[N:20]3)[CH2:15][CH2:16]2)[S:9][CH:10]=1)=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1362842,6-DifluorobenzaldehydeHCID 67433897HCID 67433897, compound

Product 1

HCID 67466725HCID 67466725, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

At room temperature, a solution of sodium hydroxide (19 mg) in methanol (0.25 ml) and water (0.05 ml) was added to a solution of 1-[4-(4-acetyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (190 mg) and 2,6-difluorobenzaldehyde (67 mg) in methanol (0.12 ml). The reaction mixture was stirred at room temperature overnight. After aqueous work-up, the mixture was extracted with ethyl acetate and the extracts were dried with sodium sulphate and concentrated under reduced pressure. The residue was purified chromatographically. This gave (2E)-3-(2,6-difluorophenyl)-1-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]prop-2-en-1-one (160 mg).

Workup

  1. extractionAfter aqueous work-up, the mixture was extracted with ethyl acetate
  2. dry with materialthe extracts were dried with sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-122e1405889f46368bb82ffa7a3b7215
Source dataset
uspto-grants-2015_12
Patent number
US09220266B2

Reaction notes

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