3-(2-Chlorophenyl)propanoic acid → N-(3-{3-[3-(2-chlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428986

반응식

HRID 428986 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:36][C:37]1([C:43]2[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:46]=[CH:47][CH:48]=2)[CH:42]2[CH:38]1[CH2:39][NH:40][CH2:41]2.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([N:40]1[CH2:41][CH:42]2[CH:38]([C:37]2([C:43]2[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:46]=[CH:47][CH:48]=2)[CH3:36])[CH2:39]1)=[O:12]

참가 물질

7

반응물 5

HCID 956763-(2-Chlorophenyl)propanoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

생성물 1

HCID 22141174N-(3-{3-[3-(2-chlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide수율 109.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(2-chlorophenyl)propanoic acid (200 mg, 1.08 mmol) in N,N-dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (187 mg, 1.22 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (318 mg, 1.66 mmol). After stirring at room temperature for 10 min, the mixture was treated with the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 400 mg, 1.32 mmol) and sodium hydrogen carbonate (200 mg, 2.38 mmol). The reaction mixture was stirred at room temperature for 3 d and then concentrated in vacuo. Water (15 ml) was added and the reaction mixture was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (10 ml), dried (MgSO4), and concentrated in vacuo to afford 510 mg of a light brown oil. Sonication for 5 min at room temperature in dichloromethane (5 ml) followed by filtration afforded the title compound as an off-white solid (124 mg, 27%).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 3 d
  2. concentrationconcentrated in vacuo
  3. additionWater (15 ml) was added
  4. extractionthe reaction mixture was extracted with ethyl acetate (2×20 ml)
  5. washThe combined organic extracts were washed with water (10 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-22c761bee6084d5d848f8b00ad29b49d
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313312B1

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