Lithium cyclopropylmethoxide → 6-(4-chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

HRID 416467Notes

Reaction equation

HRID 416467 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[C:16]([C:17]([F:20])([F:19])[F:18])=[N:15][C:14](Br)=[C:13]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:12]=1)=[O:10].[CH:29]1([CH2:32][O-:33])[CH2:31][CH2:30]1.[Li+]>O1CCCC1>[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[C:16]([C:17]([F:20])([F:19])[F:18])=[N:15][C:14]([O:33][CH2:32][CH:29]2[CH2:31][CH2:30]2)=[C:13]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 20660854Lithium cyclopropylmethoxideHCID 462210855-bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Product 1

HCID 444665706-(4-chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.048 g 5-bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide was added 1 ml of a 0.25 M solution of lithium cyclopropylmethoxide in tetrahydrofuran and the mixture was stirred at room temperature for 30 min. The orange reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine. After evaporation the crystalline residue was triturated under methanol to yield 0.028 g of the title compound as white crystals. MS (M−H) at 468.2.

Workup

  1. customThe orange reaction mixture was partitioned between 10% citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. customAfter evaporation the crystalline residue
  5. customwas triturated under methanol

Sources & evidence

ORD record
ord-7c40172b6d574eaea7a8dfe0c1283b67
Source dataset
uspto-grants-2012_01
Patent number
US08088920B2

Reaction notes

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