1,3-Dichloroacetone → HCID 178423966, compound

HRID 1094039Notes

Reaction equation

HRID 1094039 reaction equation
Cl[CH2:2][C:3]([CH2:5]Cl)=O.F[C:8](F)(F)[C:9]1[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=1.[CH3:18]CN(C(C)C)C(C)C.C[N:28]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[NH:30][C:29]1=[S:39]>COCCOC.CN(C=O)C>[CH3:2][C:3]1[N:15]2[CH:10]=[C:9]([CH:8]([S:39][C:29]3[NH:28][CH:32]=[C:31]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:30]=3)[CH3:18])[N:14]=[C:13]2[CH:12]=[CH:11][CH:5]=1

Participants

7

Reactant 4

HCID 107931,3-DichloroacetoneHCID 81531DiisopropylethylamineHCID 8210242-Amino-6-(trifluoromethyl)pyridineHCID 201464331-Methyl-4-phenyl-1,3-dihydroimidazole-2-thione

Product 1

HCID 178423966HCID 178423966, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,3-dichloroacetone (0.01 mL, 0.11 mmol) was added dropwise to a solution of 6-trifluoromethyl-pyridin-2-ylamine (0.016 g, 0.10 mmol) in 1,2-dimethoxyethane (1.0 mL), and the mixture was left to stir at room temperature for 2 h. The solvent was removed in vacuo and the resulting residue re-dissolved in ethanol (1.0 mL). The reaction mixture was subsequently heated under reflux for 2 h, and the solvent was removed under reduced pressure. DIPEA (0.05 mL, 0.25 mmol) and 1-methyl-4 phenyl-1,3-dihydro-imidazole-2-thione (0.017 g, 0.09 mmol) were sequentially added to a solution of the crude product in DMF (1.0 mL). The reaction mixture was then heated at 60° C. for 2 h after which LC-MS showed complete consumption of the starting materials. The solvent was removed under reduced pressure and the crude product purified using preparative LC-MS to yield the title compound. LC-MS: m/z=389.1 (MH+), tR=0.52 min, method C.

Workup

  1. waitthe mixture was left
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting residue re-dissolved in ethanol (1.0 mL)
  4. temperatureThe reaction mixture was subsequently heated
  5. temperatureunder reflux for 2 h
  6. customthe solvent was removed under reduced pressure
  7. temperatureThe reaction mixture was then heated at 60° C. for 2 h after which LC-MS
  8. customconsumption of the starting materials
  9. customThe solvent was removed under reduced pressure
  10. customthe crude product purified

Sources & evidence

ORD record
ord-fe5699911c3540b384882c9eabf4a6b4
Source dataset
uspto-grants-2012_03
Patent number
US08133897B2

Reaction notes

Loading…