Hydrochloric Acid → HCID 86676328, compound

HRID 1023026Notes

Reaction equation

HRID 1023026 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:14]1[N:15]=[C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:37])[CH2:26][N:27]3[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[N:28]3)[CH2:21][CH2:20]2)[S:17][CH:18]=1)=[N:12][OH:13].[C:38](Cl)(=[O:40])[CH3:39].C(N(CC)CC)C.Cl>ClCCl>[C:38]([O:13][N:12]=[C:11]([C:14]1[N:15]=[C:16]([CH:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:37])[CH2:26][N:27]3[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:35])([F:36])[F:34])=[N:28]3)[CH2:23][CH2:24]2)[S:17][CH:18]=1)[CH:10]=[CH:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])(=[O:40])[CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 76143542HCID 76143542, compound2×

Product 1

HCID 86676328HCID 86676328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 1-oxime (i.e. the product of Example 2, Step B) (0.10 g, 0.189 mmol), acetyl chloride (0.017 g, 0.22 mmol) and triethylamine (0.022 g, 0.22 mmol) in dichloromethane (5 mL) was stirred for 2 hr and shaken with 1 mL of 1 N hydrochloric acid. The mixture was poured onto a Celite® extraction tube, eluted with dichloromethane and concentrated to give 0.11 g of crude material which was purified via silica gel chromatography (hexanes-ethyl acetate gradient) to provide 0.11 g of the title compound.

Workup

  1. additionThe mixture was poured onto a Celite® extraction tube
  2. washeluted with dichloromethane
  3. concentrationconcentrated
  4. customto give 0.11 g of crude material which
  5. customwas purified via silica gel chromatography (hexanes-ethyl acetate gradient)

Sources & evidence

ORD record
ord-8f556eb3e3d24ddc9fb9694cf43b7dbb
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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