Diisopropylethylamine → HCID 86616966, compound

HRID 1865885Notes

Reaction equation

HRID 1865885 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:19](O)=[O:20])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.ClC(N(C)C)=C(C)C.[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37].C(N(C(C)C)C(C)C)C>ClCCl>[OH:37][C@@H:32]1[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]1[NH:30][C:19]([C:5]1[CH:4]=[N:3][C:2]([Br:1])=[C:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=2)[N:6]=1)=[O:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 86616969HCID 86616969, compound

Product 1

HCID 86616966HCID 86616966, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (0.0028 mol) of 5-bromo-6-(4-trifluoromethoxy-phenyl)-pyrazine-2-carboxylic acid in 80.0 ml dichloromethane was added at room temperature 0.4 ml (0.405 g 0.0030 mol) (1-chloro-2-methyl-propenyl)-dimethyl-amine and the mixture was stirred for 0.5 hours. To the resulting dark solution was added 0.35 g (0.0030 mol) (1R,2R)-2-amino-cyclohexanol and 0.94 ml (0.712 g, 0.0060 mol) N-ethyldiisopropylamine and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase washed with 10% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of 100% heptane to heptane with 40% ethyl acetate to yield 1.107 g of the tile compound as a white waxy solid. MS (ISP) (M+H+)=360.0 and 362.0.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe reaction mixture was then partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase washed with 10% aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel with a gradient of 100% heptane to heptane with 40% ethyl acetate

Sources & evidence

ORD record
ord-207e579023a2441a8552c4839f26a456
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

Loading…