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

HRID 586790

반응식

HRID 586790 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4ea4f38997dd4427b20ebededd071221
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936736B2

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