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Citric Acid → HCID 24856502, 화합물

HRID 1159221
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HRID 1159221 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

HCID 24856502HCID 24856502, 화합물수율 41.7%

시약·촉매·용매

2
HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a41874be452a40919d3152e984c0c3a6
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07812028B2

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