Dimethylformamide → N-(3-{3-[3-(5-fluoro-3-methyl-1H-indol-2-yl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428984노트

반응식

HRID 428984 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][C:13]([OH:15])=O)=[C:5]2[CH3:16].O.O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2N=N1.Cl.CN(C)[CH2:31][CH2:32][CH2:33]N=C=NCC.[CH3:40][S:41](N)(=[O:43])=[O:42].[C:45](=O)([O-])O.[Na+].[CH3:50][N:51]([CH3:54])C=O>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][C:13]([N:51]1[CH2:54][CH:33]3[CH:45]([C:32]3([C:25]3[CH:24]=[C:23]([NH:19][S:41]([CH3:40])(=[O:43])=[O:42])[CH:22]=[CH:27][CH:26]=3)[CH3:31])[CH2:50]1)=[O:15])=[C:5]2[CH3:16]

참가 물질

7

반응물 6

HCID 6228DimethylformamideHCID 72879MethanesulfonamideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 221411665-fluoro-3-methyl-1H-indole-2-propanoic acid

생성물 1

HCID 22141190N-(3-{3-[3-(5-fluoro-3-methyl-1H-indol-2-yl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

실험 절차

To a solution of 3-(5-fluoro-3-methyl-1H-indol-2-yl)propanoic acid (prepared according to the method described in EP 510398 A2, 200 mg, 0.90 mmol) in N,N-dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (154 mg, 1.00 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (262 mg, 1.36 mmol). After stirring at room temperature for 10 min, the mixture was treated with the hydrochloride salt of N-13-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 308 mg, 0.90 mmol) and sodium hydrogen carbonate (150 mg, 1.80 mmol). The reaction mixture was stirred at room temperature overnight before concentrating 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 (15 ml), dried (MgSO4), and concentrated in vacuo to afford 350 mg of a brown viscous oil which was not purified further.

후처리

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationbefore concentrating 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 (15 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0a6ef66b6b4748f7a1fb0a07c066f029
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313312B1

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