Piperidine → HCID 66607341, compound

HRID 2365114Notes

Reaction equation

HRID 2365114 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:23][CH3:24])[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2[NH:16][C:17]([CH:20]=O)=[C:18]([CH3:19])[C:12]=2[C:11]1=[O:22])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)N[C:31](=[O:36])[CH2:30]2.N1CCCC[CH2:38]1>C(O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:23][CH3:24])[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2[NH:16][C:17]([CH:20]=[C:30]3[C:29]4[C:33](=[CH:34][CH:35]=[C:27]([F:26])[CH:28]=4)[CH2:38][C:31]3=[O:36])=[C:18]([CH3:19])[C:12]=2[C:11]1=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 86637687HCID 86637687, compound

Product 1

HCID 66607341HCID 66607341, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of ethyl-[2-(2-formyl-3-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-5-yl)-ethyl]-carbamic acid tert-butyl ester (160 mg, 0.458 mmol), 5-fluoro-1,3-dihydro-indol-2-one (65.76 mg, 0.435 mmol), in. 0.803 ml of ethanol was added dropwise with anhydrous piperidine (0.022 ml). The mixture was stirred overnight at room temperature until a precipitate was formed. The precipitate was filtered under reduced pressure and washed with ethanol (0.3 ml×3) to give ethyl-{2-[2-(6-fluoro-2-oxo-indan-1-ylidenemethyl)-3-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-5-yl]ethyl}-carbamic acid tert-butyl ester (111 mg, 50%) as a yellow solid.

Workup

  1. customwas formed
  2. filtrationThe precipitate was filtered under reduced pressure
  3. washwashed with ethanol (0.3 ml×3)

Sources & evidence

ORD record
ord-a1a788a015c848db8622368e831df5c8
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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