O-Methylhydroxylamine hydrochloride → HCID 86676329, compound

HRID 1023027Notes

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.[CH3:38][O:39][NH2:40]>CO>[CH3:38][O:39][N:40]=[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:33])([F:34])[F:35])=[N:27]3)[CH2:20][CH2:19]2)[S:16][CH:17]=1)[CH:10]=[CH:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8]

Participants

Conditions

Temperature: 60 °C

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) and methoxyamine hydrochloride (0.047 g, 0.58 mmol) in methanol (10 mL) was heated overnight at 60° C. The reaction was concentrated under reduced pressure, partitioned between dichloromethane and saturated sodium bicarbonate. The mixture was eluted from a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge) with dichloromethane and concentrated to provide 0.26 g of the title compound.

Workup

concentrationThe reaction was concentrated under reduced pressure
custompartitioned between dichloromethane and saturated sodium bicarbonate
washThe mixture was eluted from a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge) with dichloromethane
concentrationconcentrated

Sources & evidence

ORD record: ord-734f15aa09684d4eb9d8ea3d559a6175
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722678B2

Reaction notes

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