4-Methylpiperidine → 4-Methyl-piperidine-1-carboxylic acid {4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-amide

HRID 502259Notes

Reaction equation

HRID 502259 reaction equation
COC1C=CC([O:9][C:10](=O)[NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]([CH:34]4[CH2:37][CH2:36][CH2:35]4)[C:20]4[C:25]([C:26]=3[C:27]#[N:28])=[CH:24][CH:23]=[C:22]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=4)=[CH:14][CH:13]=2)=CC=1.[CH3:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl>[C:27]([C:26]1[C:25]2[C:20](=[CH:21][C:22]([O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:23][CH:24]=2)[N:19]([CH:34]2[CH2:35][CH2:36][CH2:37]2)[C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10]([N:43]2[CH2:44][CH2:45][CH:40]([CH3:39])[CH2:41][CH2:42]2)=[O:9])=[CH:13][CH:14]=1)#[N:28]

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 59426020{4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-carbamic acid 4-methoxy-phenyl ester

Product 1

HCID 594258994-Methyl-piperidine-1-carboxylic acid {4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-amideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[3-cyano-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indol-2-yl]-phenyl}-carbamic acid 4-methoxy-phenyl ester (40 mg, 0.082 mmol) in DCM (4 mL) is added 4-methylpiperidine (0.16 mmole) and the reaction is stirred for 18 h at reflux temperature. The solvent is removed under reduced pressure. The residue is dissolved in EtOAc and then triturated with hexane. The precipitate is collected by filtration and washed with 50% EtOAc/hexane and dried in vacuo to afford 4-methyl-piperidine-1-carboxylic acid {4-[3-cyano-1-cyclobutyl-6-(2-methoxyethoxy)-1H-indol-2-yl]-phenyl}-amide, compound 1377, (26 mg, 68%).

Workup

  1. temperatureat reflux temperature
  2. customThe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in EtOAc
  4. customtriturated with hexane
  5. filtrationThe precipitate is collected by filtration
  6. washwashed with 50% EtOAc/hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fc4a23e9a8c34b60ab96f7fffc868492
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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