Diisopropylethylamine → HCID 86616965, compound

HRID 1865881Notes

Reaction equation

HRID 1865881 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14](Br)=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)[N:12]=1)=[O:10].Cl.[CH:30]1([NH:33][CH3:34])[CH2:32][CH2:31]1.C(N(C(C)C)C(C)C)C>CS(C)=O>[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([N:33]([CH:30]2[CH2:32][CH2:31]2)[CH3:34])=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)[N:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18546974N-methylcyclopropanamine hydrochlorideHCID 86616966HCID 86616966, compound

Product 1

HCID 86616965HCID 86616965, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.052 g of 5-bromo-6-(4-trifluoromethoxy-phenyl)-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide in 2 ml dimethylsulfoxide was added at room temperature 0.024 g of cyclopropyl-methyl-amine hydrochloride and 0.04 ml N-ethyldiisopropylamine. The mixture was stirred at room temperature for 72 hours. The reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic layer washed with 10% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel to yield 0.033 g (61% yield) of the title compound as colorless oil. MS (ISP) (M+H+)=451.1.

Workup

  1. customThe reaction mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic layer washed with 10% aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4ad5685f2dd64809b14cf92c9fc49593
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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