Piperidine → HCID 178510683, compound

HRID 447528Notes

Reaction equation

HRID 447528 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[N:8][NH:9]2)=[CH:5][CH:4]=1)=O.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23].N1CCCCC1>CCO>[O:23]=[C:15]1[NH:14][C:22]2[C:17](/[C:16]/1=[CH:1]\[C:3]1[CH:11]=[C:10]3[C:6]([C:7]([C:12]#[N:13])=[N:8][NH:9]3)=[CH:5][CH:4]=1)=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 768462446-formyl-1H-indazole-3-carbonitrile

Product 1

HCID 178510683HCID 178510683, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 6-formyl-1H-indazole-3-carbonitrile (1.10 g, 6.4 mmol) and 2-oxindole (871 mg, 6.5 mmol) in EtOH (25 mL) was added piperidine (0.1 mL, 1 mmol). The resulting mixture was refluxed (oil temp. 75° C.) for 90 min, then cooled to rt. The resulting precipitate was collected by suction filtration and dried to give the title compound as an orange solid (1.5 g, 82%) 1H NMR (400 MHz, DMSO-d6) δ 14.6 (s, 1H), 10.66 (s, 1H), 8.09 (s, 1H), 8.01 (d, J=8.5 Hz, 1H) 7.78 (s, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.48 (d, 1H, J=7.8 Hz), 7.24 (t, J=7.6 Hz, 1H), 6.88 (d, J=7.8 Hz, 1H), 6.83 (t, J=7.8 Hz, 1H).

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting precipitate was collected by suction filtration
  3. customdried

Sources & evidence

ORD record
ord-661fab6afa264f828ec4e26b8951caac
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

Loading…