Water → HCID 63586295, compound

HRID 1747493Notes

Reaction equation

HRID 1747493 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.Cl[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=1.O>CN(C=O)C>[CH3:29][O:28][C:24]1[N:23]=[C:22]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 870092-Chloro-6-methoxypyridine

Product 1

HCID 63586295HCID 63586295, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (2.16 mL, 12.7 mmol) was added to a solution of ethyl piperidine-4-carboxylate (2.00 g, 12.7 mmol) and 2-chloro-6-methoxypyridine (1.48 mL, 12.7 mmol) in DMF (10 mL), and the mixture was stirred while irradiated with microwaves at 150° C. for 3 hours using Initiator® manufactured by Biotage Japan Ltd. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=90/10] to obtain the title compound (365 mg, yield: 11%).

Workup

  1. customwhile irradiated with microwaves at 150° C. for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=90/10]

Sources & evidence

ORD record
ord-f9a006ff801a43cea14b40c4794fa0c3
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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