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 2388673Notes

Reaction equation

HRID 2388673 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3fca1cf5818241bdaa791cc11ae3ba63
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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