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Ammonium Chloride → Ethyl 3-{[(5-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridin-2-yl)carbonyl](methyl)amino}propanoate

HRID 2091067
ノート
印刷プレビュー

反応式

HRID 2091067 の反応式
C1([CH:7]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([OH:28])=O)=[N:24][CH:25]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])CCCCC1.[CH3:29][NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].O.ON1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[CH:43]1([CH:7]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([N:30]([CH3:29])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:28])=[N:24][CH:25]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667777375-{[Cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridine-2-carboxylic acid

生成物 1

HCID 66777498
Ethyl 3-{[(5-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridin-2-yl)carbonyl](methyl)amino}propanoate
収率 82%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a mixture of 5-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridine-2-carboxylic acid (300 mg) synthesized in Example A55(2), ethyl 3-(methylamino)propanoate (155 mg), 1-hydroxybenzotriazole monohydrate (181 mg), triethylamine (328 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (226 mg), and the mixture was stirred at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20-60% ethyl acetate/hexane) to give the title object compound (318 mg, 82%) as a pale-yellow oil.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20-60% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6d7636ea27b44d289f071e874a7ece67
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436043B2

反応ノート

読み込み中…

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