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Thionyl Chloride → HCID 178522090, 화합물

HRID 2223370
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HRID 2223370 반응식
S(Cl)(Cl)=O.[NH2:5][C:6]1[C:7]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)=[O:17])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[O:26]=[C:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C@H:32]1[CH2:37][CH2:36][C@H:35]([C:38](O)=[O:39])[CH2:34][CH2:33]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]([C:7]2[C:6]([NH:5][C:38]([C@H:35]3[CH2:36][CH2:37][C@H:32]([N:28]4[CH2:29][CH2:30][CH2:31][C:27]4=[O:26])[CH2:33][CH2:34]3)=[O:39])=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[O:17])=[N:20][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231250193-amino-N-(5-chloropyridin-2-yl)-2-naphthamideHCID 178516220HCID 178516220, 화합물

생성물 1

HCID 178522090HCID 178522090, 화합물
수율 70.4%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

Trans-4-(2-oxopyrrolidin-1-yl)cyclohexane-carboxylic acid (40 mg) obtained in Reference Example 2 is dissolved in chloroform (3 ml), and thereto are added thionyl chloride (15 μl) and N,N-dimethylformamide (1 drop) followed by stirring at room temperature for 15 hours. To the reaction solution are added 3-amino-N-(5-chloropyridin-2-yl)-2-naphthamide (31 mg) obtained in Example 34(1) and pyridine (1 ml), and the mixture is stirred at room temperature for 12 hours. After adding trans-4-(2-oxopyrrolidin-1-yl)cyclohexanecarboxylic acid (43 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (42 mg) and 4-(dimethylamino)pyridine (56 mg), the mixture is stirred at room temperature for another 12 hours. To the reaction solution is poured saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The extract is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then 1/4) to give title compound (36 mg).

후처리

  1. stirringthe mixture is stirred at room temperature for 12 hours
  2. stirringthe mixture is stirred at room temperature for another 12 hours
  3. extractionthe mixture is extracted with chloroform
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-7a60568a9b0a411e85c391df41237b67
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375119B2

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