Citric Acid → HCID 24856502, compound

HRID 1929825Notes

Reaction equation

HRID 1929825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[N:10][C:9]=1[N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(C(C)C)C(C)C)C.Cl.[NH2:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[OH:51].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C>[OH:51][C@@H:46]1[CH2:47][CH2:48][CH2:49][CH2:50][C@H:45]1[NH:44][C:14]([C:12]1[CH:11]=[N:10][C:9]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:13]=1)=[O:16]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 67505404HCID 67505404, compound

Product 1

HCID 24856502HCID 24856502, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.10 g 6-(2-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid in 3.0 ml of DMF is added at room temperature 0.082 g 1,1′-carbonyl-diimidazole, 0.22 ml N-ethyldiisopropylamine and 0.057 g (1R,2R)-2-amino-cyclohexanol hydrochloride and stirred for 72 hours. To the mixture is added citric acid 10% solution and ethyl acetate. The organic layer is washed with sodium bicarbonate 10% solution and sodium chloride saturated solution. The organic layer is separated and dried over sodium sulfate and evaporated at the rotary evaporator. The residue is purified by chromatography on silica gel with heptane/ethyl acetate 40/60 to yield 0.055 g of the title compound as white solid, MS (ISP) 401.3 (M+H)+.

Workup

  1. washThe organic layer is washed with sodium bicarbonate 10% solution and sodium chloride saturated solution
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated at the rotary evaporator
  5. customThe residue is purified by chromatography on silica gel with heptane/ethyl acetate 40/60

Sources & evidence

ORD record
ord-2f97789d631441ecb42c4cc15c8ef292
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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