N-Methylpiperidine → HCID 59711081, compound

HRID 2221363Notes

Reaction equation

HRID 2221363 reaction equation
CN1CCCCC1.[CH3:8][C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.[NH2:19][CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:30][C:31]([NH:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)=[O:32])[CH:28]=2)[O:23][C:22]([CH3:43])([CH3:42])[CH:21]1[OH:44]>ClCCl>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][NH:33][C:31](=[O:32])[CH2:30][C:27]2[CH:28]=[C:29]3[C:24](=[CH:25][CH:26]=2)[O:23][C:22]([CH3:43])([CH3:42])[CH:21]([OH:44])[CH:20]3[NH:19][S:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([CH3:8])[CH:10]=2)(=[O:17])=[O:16])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 12291N-MethylpiperidineHCID 27345953-Methylbenzenesulphonyl chlorideHCID 69058857HCID 69058857, compound

Product 1

HCID 59711081HCID 59711081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15 mg PS-methylpiperidine and a solution of 6.0 mg 3-methylbenzenesulfonyl chloride in 0.5 ml dichloromethane were added in succession in a sample well of a sample plate for automatic parallel synthesis to a solution of 9 mg of the 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-4-chlorobenzyl acetamide obtained above in 0.5 ml dichloromethane. The sample plate was shaken for 40 hours at room temperature, and then 20 mg AMPS was added to the well. The plate was shaken for a further 16 hours at room temperature before the liquid reaction phase was separated from the resin, and the resin was washed twice with 1 ml portions of dichloromethane. The solvent of the combined organic phases was evaporated at reduced pressure, and the title compound was obtained in a purity of 95% (determination by HPLC-MS), [M+H]+ 529.

Workup

  1. addition20 mg AMPS was added to the well
  2. stirringThe plate was shaken for a further 16 hours at room temperature before the liquid reaction phase
  3. customwas separated from the resin
  4. washthe resin was washed twice with 1 ml portions of dichloromethane
  5. customThe solvent of the combined organic phases was evaporated at reduced pressure

Sources & evidence

ORD record
ord-4eaa86c54f5a43619f5e69af4624efb3
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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