Diisopropylethylamine → HCID 118308044, compound

HRID 1750495Notes

Reaction equation

HRID 1750495 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([N:19]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[NH:25][CH3:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:27]([N:19]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@H:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[N:25]([CH3:26])[C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 189876452-Chloro-5-(trifluoromethyl)pyrazineHCID 118308200HCID 118308200, compound

Product 1

HCID 118308044HCID 118308044, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 198 mg, 1.087 mmol), (1S,2S)-1-N,1-N-dibenzyl-2-N-methylcyclopentane-1,2-diamine (291 mg, 0.988 mmol) and DIPEA (518 μl, 2.97 mmol) in DMSO (3.3 ml) was subjected to microwave irradiation at 140° C. for 4 hours. The reaction was diluted with ethyl acetate (20 ml), washed with a saturated solution of sodium bicarbonate (3×20 ml), brine (20 ml), filtered through a hydrophobic frit and concentrated in vacuo. This was then purified by column chromatography (silica, 0-15% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customirradiation at 140° C. for 4 hours
  2. washwashed with a saturated solution of sodium bicarbonate (3×20 ml), brine (20 ml)
  3. filtrationfiltered through a hydrophobic frit
  4. concentrationconcentrated in vacuo
  5. customThis was then purified by column chromatography (silica, 0-15% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-bccf63cd745f452ba8ca14c7d80cc9d1
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…