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Thionyl Chloride → HCID 178522090、化合物

HRID 2223370
ノート
印刷プレビュー

反応式

HRID 2223370 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 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、化合物

生成物 1

HCID 178522090HCID 178522090、化合物
収率 70.4%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a60568a9b0a411e85c391df41237b67
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07375119B2

反応ノート

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