Hydroxyamine hydrochloride → HCID 76143542, compound

HRID 1023025Notes

Reaction equation

HRID 1023025 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.Cl.[NH2:38][OH:39]>CO>[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)=[N:38][OH:39]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67470591HCID 67470591, compound2×

Product 1

HCID 76143542HCID 76143542, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 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) (0.5 g, 0.93 mmol) and hydroxylamine hydrochloride (0.078 g, 1.14 mmol) in methanol (10 mL) was heated at reflux for 2 h. The reaction mixture was concentrated under reduced pressure and partitioned between dichloromethane and saturated sodium bicarbonate. The mixture was poured onto a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge), eluted with dichloromethane and concentrated to provide 0.5 g of the title compound.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between dichloromethane and saturated sodium bicarbonate
  4. additionThe mixture was poured onto a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge)
  5. washeluted with dichloromethane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be75578f00624c75b88eaeb486bad624
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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