Diisopropylethylamine → 1-(4-Ethyl-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butan-1-one

HRID 2388673노트

반응식

HRID 2388673 반응식
C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH2:34]([CH:36]1[C:41]2[CH:42]=[CH:43][S:44][C:40]=2[CH2:39][CH2:38][NH:37]1)[CH3:35].[CH3:45][O:46][C:47]1[CH:52]=[C:51]([CH3:53])[C:50]([S:54]([N:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH:58]2[CH2:63][CH2:64][CH2:65][C:66](O)=[O:67])(=[O:56])=[O:55])=[C:49]([CH3:69])[CH:48]=1>C(=O)(O)[O-].[Na+]>[CH2:34]([CH:36]1[C:41]2[CH:42]=[CH:43][S:44][C:40]=2[CH2:39][CH2:38][N:37]1[C:66](=[O:67])[CH2:65][CH2:64][CH2:63][CH:58]1[CH2:59][CH2:60][CH2:61][CH2:62][N:57]1[S:54]([C:50]1[C:51]([CH3:53])=[CH:52][C:47]([O:46][CH3:45])=[CH:48][C:49]=1[CH3:69])(=[O:56])=[O:55])[CH3:35]

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 162551044-Ethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochlorideHCID 574771724-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid

생성물 1

HCID 442524131-(4-Ethyl-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butan-1-one

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

N-Ethyldiisopropylamine (0.21 ml, 1.218 mmol), 1-hydroxybenzotriazole hydrate (60 mg, 0.447 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (116 mg, 0.609 mmol) and 4-ethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (123 mg, 0.609 mmol) were added to a solution of 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic acid (AC7) (0.15 g, 0.406 mmol) in MC (10 ml) and the mixture was stirred at room temperature for 15 hours. Saturated sodium bicarbonate solution (20 ml) was added to the mixture and the aqueous phase was then extracted with MC (2×30 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1. The yield was 200 mg (94%, white, resin).

후처리

  1. extractionthe aqueous phase was then extracted with MC (2×30 ml)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1

출처 및 근거

ORD 기록
ord-3fca1cf5818241bdaa791cc11ae3ba63
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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