Piperidine → HCID 10280590, compound

HRID 1359695Notes

Reaction equation

HRID 1359695 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11]([CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])(=[O:13])=[O:12])[CH:8]=2)[NH:3]1.[CH3:23][C:24]1[C:28]([C:29]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)=[O:30])=[C:27]([CH3:38])[NH:26][C:25]=1[CH:39]=O.N1CCCCC1>C(O)C>[CH3:23][C:24]1[C:28]([C:29]([N:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]2)=[O:30])=[C:27]([CH3:38])[NH:26][C:25]=1/[CH:39]=[C:10]1\[C:2](=[O:1])[NH:3][C:4]2[C:9]\1=[CH:8][C:7]([S:11]([CH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18])(=[O:12])=[O:13])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 121115823,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeHCID 18179730HCID 18179730, compound

Product 1

HCID 10280590HCID 10280590, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(2-oxo-2,3-dihydro-1H-indole-5-sulfonylmethyl)-benzonitrile (100 mg, 0.32 mmol) and 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (79 mg, 0.32 mmol) in ethanol (4 mL) was added piperidine (0.1 mL). The reaction mixture was stirred at 25° C. for three days. The solvent was evaporated and the residue was purified on a silica gel column eluting with MeOH—CH2Cl2 10:90 to provide 123 mg (71%) of 2-{3-[1-[3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonylmethyl}-benzonitrile as a pale orange solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a silica gel column
  3. washeluting with MeOH—CH2Cl2 10:90

Sources & evidence

ORD record
ord-2a7b230eb604409d9d94fcea516dbe72
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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