Triethylamine → HCID 178448482, compound

HRID 340654

Reaction equation

HRID 340654 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:16]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[S:18][C:17]1=[NH:25])[CH2:13][C:14]#[CH:15].[F:26][C:27]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:28]=1[C:29](Cl)=[O:30].C(N(CC)CC)C>C(Cl)Cl>[C:21]([C:19]1[S:18]/[C:17](=[N:25]\[C:29](=[O:30])[C:28]2[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:27]=2[F:26])/[N:16]([CH2:12][CH2:13][C:14]#[CH:15])[CH:20]=1)([CH3:22])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 86644542HCID 86644542, compound

Product 1

HCID 178448482HCID 178448482, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine p-toluenesulfonate (prepared as described in US20080242654) (2.6 g, 6.83 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl chloride (1.55 g, 6.83 mmol) in anhydrous CH2Cl2 (30 mL) was treated dropwise at 0° C. with triethylamine (1.91 mL, 1.38 mmol). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with hexane-EtOAc (2:1) to afford 2.5 g of the title compound. MS (DCI/NH3) m/z 399 (M+H)+.

Workup

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with hexane-EtOAc (2:1)

Sources & evidence

ORD record
ord-fa000a7de4b846c38da818ad1adff5b8
Source dataset
uspto-grants-2014_11
Patent number
US08895592B2

Linked notes

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