Citric Acid → HCID 24856502, compound

HRID 1159221Notes

Reaction equation

HRID 1159221 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-a41874be452a40919d3152e984c0c3a6
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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