Piperidine → HCID 68896682, compound

HRID 897286Notes

Reaction equation

HRID 897286 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:13][O:14][C:15]([C:17]1[C:26]([O:27][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:29])=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[N:24]2)=[C:19]([C:36]#[C:37][CH2:38]OS(C)(=O)=O)[N:18]=1)=[O:16]>C(#N)C>[CH3:13][O:14][C:15]([C:17]1[C:26]([O:27][C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:29])=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[N:24]2)=[C:19]([C:36]#[C:37][CH2:38][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 86600103HCID 86600103, compound

Product 1

HCID 68896682HCID 68896682, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of piperdine (207 μL, 2.09 mmol) and potassium carbonate (296 mg, 2.14 mmol) in dry acetonitrile (10 mL) was pipetted in 5-(3-methanesulfonyloxy-prop-1-ynyl)-8-(1-phenyl-methanoyloxy)-[1,6]naphthyridine-7-carboxylic acid methyl ester (230 mg, 0.522 mmol) in acetonitrile (1 mL) and the mixture was stirred at room temperature for 3 hours. The reaction was concentrated, filtered, and purified on the Gilson auto-prep running a 95-50% H2O (0.1% TFA)/CH3CN (0.09% TFA) gradient over 30 minutes to obtain the desired compound as a light brown oil.

Workup

  1. concentrationThe reaction was concentrated
  2. filtrationfiltered
  3. custompurified on the Gilson auto-prep
  4. customover 30 minutes

Sources & evidence

ORD record
ord-ce2a888dfeec4cb5929c9cd4550e1212
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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