Ammonium Chloride → HCID 67470600, compound

HRID 1023028Notes

Reaction equation

HRID 1023028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[CH:10][C:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:36])[CH2:25][N:26]3[C:30]([CH3:31])=[CH:29][C:28]([C:32]([F:35])([F:34])[F:33])=[N:27]3)[CH2:20][CH2:19]2)[S:16][CH:17]=1)=[O:12].[Cl-].[NH4+]>C(O)C.[Zn]>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH2:9][CH2:10][C:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:36])[CH2:25][N:26]3[C:30]([CH3:31])=[CH:29][C:28]([C:32]([F:34])([F:35])[F:33])=[N:27]3)[CH2:22][CH2:23]2)[S:16][CH:17]=1)=[O:12]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67470591HCID 67470591, compound2×

Product 1

HCID 67470600HCID 67470600, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2,6-difluorophenyl)-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-2-propen-1-one (i.e. the product of Example 2, Step A) (0.25 g, 0.48 mmol), zinc dust (0.25 g, 3.8 mmol) and saturated ammonium chloride (0.25 mL) in ethanol (5 mL) was stirred overnight, concentrated to dryness, treated with dichloromethane and filtered. The filtrate was concentrated and purified via silica gel chromatography (hexanes: ethyl acetate gradient) to provide 0.025 g of 3-(2,6-difluorophenyl)-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-1-propanone.

Workup

  1. concentrationconcentrated to dryness
  2. additiontreated with dichloromethane
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified via silica gel chromatography (hexanes: ethyl acetate gradient)

Sources & evidence

ORD record
ord-aa60aba9499c439198b5c8e837a2982a
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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