Piperidine → HCID 67398768, compound

HRID 70701Notes

Reaction equation

HRID 70701 reaction equation
Cl.C(N=C=N[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])C)C.ON1C2C=CC=CC=2N=N1.[C:23]([C:27]1[CH:32]=[CH:31][C:30](/[C:33](/[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([O:45][CH3:46])[N:39]=2)=[CH:34]\[C:35](O)=[O:36])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].N1CCCCC1>CN(C)C=O.C(OCC)(=O)C>[C:23]([C:27]1[CH:28]=[CH:29][C:30](/[C:33](/[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([O:45][CH3:46])[N:39]=2)=[CH:34]\[C:35]([N:10]2[CH2:9][CH2:8][CH2:7][CH2:12]2)=[O:36])=[CH:31][CH:32]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58452337(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-enoic acid

Product 1

HCID 67398768HCID 67398768, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (80 mg) and 1-hydroxybenzotriazole (61 mg) were added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-enoic acid obtained in Reference Example 4-6 (137 mg) in N,N-dimethylformamide (2 mL), and the mixture was stirred for 15 minutes. Thereafter, piperidine (50 mg) was added and the mixture was stirred at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate. This was sequentially washed with saturated aqueous sodium bicarbonate, water and brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1) to give (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)-1-(pyrrolidin-1-yl)prop-2-en-1-one as a colorless oil (63 mg, 40%).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. washThis was sequentially washed with saturated aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-cce20c9969e342e6875c56f49934b71b
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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