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2-(4-Fluorophenyl)acetic acid → (4-fluorophenyl)acetic acid N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide

HRID 1009391
ノート
印刷プレビュー

反応式

HRID 1009391 の反応式
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[Cl:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]2)=[C:34]([O:44][CH3:45])[CH:33]=1)/[C:27]([NH:29][NH2:30])=[O:28].[F:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C:54]([OH:56])=[O:55])=[CH:49][CH:48]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[F:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C:54]([NH:30][N:29]2[CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]3[CH:37]=[CH:36][C:35]([N:38]4[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]4)=[C:34]([O:44][CH3:45])[CH:33]=3)/[C:27]2=[O:28])=[O:55])=[CH:49][CH:48]=1.[Cl:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]2)=[C:34]([O:44][CH3:45])[CH:33]=1)/[C:27]([NH:29][NH:30][C:54](=[O:56])[CH2:53][C:50]1[CH:49]=[CH:48][C:47]([F:46])=[CH:52][CH:51]=1)=[O:28]
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 98372-(4-Fluorophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 670671995-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid hydrazide dihydrochlorideHCID 86585896Sodium bicarbonate water

生成物 2

HCID 67067381
(4-fluorophenyl)acetic acid N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide
HCID 670674402-(4-fluorophenyl)-N-{3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-2-oxopiperidin-1-yl}acetamide

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

IPEA (0.5 mL), HOBT (128 mg) and EDC (182 mg) were added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid hydrazide dihydrochloride (200 mg) and 4-fluorophenylacetic acid (73 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for six hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 75 mg of 2-(4-fluorophenyl)-N-{3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-2-oxopiperidin-1-yl}acetamide and 217 mg of (4-fluorophenyl)acetic acid N′-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide.

後処理

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

出典と根拠

ORDレコード
ord-96a9cc406c254244a3ce5a936498723d
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973033B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート