Triethylamine → HCID 68745534, compound

HRID 238659

Reaction equation

HRID 238659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH2:9].C(N(CC)CC)C.Cl[O-].[Na+].[OH:20][N:21]=[CH:22][C:23]1[N:24]=[C:25]([CH:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:46])[CH2:35][N:36]3[C:40]([CH3:41])=[CH:39][C:38]([C:42]([F:45])([F:44])[F:43])=[N:37]3)[CH2:30][CH2:29]2)[S:26][CH:27]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:20][N:21]=[C:22]([C:23]2[N:24]=[C:25]([CH:28]3[CH2:29][CH2:30][N:31]([C:34](=[O:46])[CH2:35][N:36]4[C:40]([CH3:41])=[CH:39][C:38]([C:42]([F:45])([F:43])[F:44])=[N:37]4)[CH2:32][CH2:33]3)[S:26][CH:27]=2)[CH2:9]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 149062-ChlorostyreneHCID 23665760Sodium HypochloriteHCID 86631243HCID 86631243, compound2×

Product 1

HCID 68745534HCID 68745534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-chloro-2-ethenylbenzene (0.035 g, 0.25 mmol), triethylamine (2.5 mg, 0.025 mmol) and Clorox® aqueous sodium hypochlorite solution (1 mL, 16.1 mmol) in dichloromethane (5 mL) was added 4-[4-[(hydroxyimino)methyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine (i.e. the product of Example 2, Step C) (0.10 g, 0.25 mmol) in dichloromethane (5 mL) dropwise over 1 h at 0° C. The reaction mixture was allowed to stir for 1 h, then filtered through Celite® diatomaceous filter aid, and concentrated under reduced pressure to give an oil, which was purified by column chromatography on silica gel using 50% ethyl acetate in hexane as eluant to give 73 mg of the title compound as a white foam, melting at 115-122° C. (crystallized from methyl acetate/petroleum ether).

Workup

  1. filtrationfiltered through Celite®
  2. filtrationdiatomaceous filter aid
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil, which
  5. customwas purified by column chromatography on silica gel using 50% ethyl acetate in hexane as eluant
  6. customto give
  7. custom73 mg of the title compound as a white foam, melting at 115-122° C. (crystallized from methyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-aaf7e68db93d44ffb6098f5868039269
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Linked notes

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