Triethylamine → N-(2-Fluoro-1,1-dimethylethyl)-2,4-difluorobenzamide

HRID 586790ノート

反応式

HRID 586790 の反応式
CCN=C=NCCCN(C)C.Cl.[F:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O.Cl.[F:25][CH2:26][C:27]([NH2:30])([CH3:29])[CH3:28].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[F:25][CH2:26][C:27]([NH:30][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:14]=1[F:13])([CH3:29])[CH3:28]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 741022,4-Difluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 139352511-Fluoro-2-methylpropan-2-amine hydrochloride

生成物 1

HCID 10198515N-(2-Fluoro-1,1-dimethylethyl)-2,4-difluorobenzamide収率 44%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

WSC HCl (1.15 g, 6 mmol) was added to a mixture of 2,4-difluorobenzoic acid (0.95 g, 6 mmol), 2-fluoro-1,1-dimethylethylamine hydrochloride (J. Med. Chem., 34, 29-37(1991): 0.77 g, 6 mmol), HOBt (0.81 g, 6 mmol) and triethylamine (0.91 g, 9 mmol) in methylene chloride (15 ml), and stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with ethyl acetate and washed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine, successively, dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1) to give the title compound (0.61 g: 44%).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine
  4. dry with materialsuccessively, dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-4ea4f38997dd4427b20ebededd071221
出典データセット
uspto-grants-2005_08
特許番号
US06936736B2

反応ノート

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