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 2388673ノート

反応式

HRID 2388673 の反応式
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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3fca1cf5818241bdaa791cc11ae3ba63
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

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