Potassium Carbonate → 1'-Benzyl-2-oxo-6-(4-phenoxyphenyl)-1,2-dihydrospiro[imidazo[1,2-b]pyrazole-3,4'-piperidine]-7-carbonitrile

HRID 64354Notes

Reaction equation

HRID 64354 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([NH:20][NH2:21])([C:15]([O:17]CC)=O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO[C:24]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)=[C:25]([C:28]#[N:29])[C:26]#[N:27].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]2([N:20]3[N:21]=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:32][CH:31]=4)[C:25]([C:26]#[N:27])=[C:28]3[NH:29][C:15]2=[O:17])[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223472272-((Methoxy)(4-phenoxyphenyl)methylene)malononitrileHCID 117668154Ethyl 1-benzyl-4-hydrazinylpiperidine-4-carboxylate hydrochloride

Product 1

HCID 1369281111'-Benzyl-2-oxo-6-(4-phenoxyphenyl)-1,2-dihydrospiro[imidazo[1,2-b]pyrazole-3,4'-piperidine]-7-carbonitrileYield 58.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 1-benzyl-4-hydrazinylpiperidine-4-carboxylate hydrochloride (350 mg, 1.0 mmol), 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile (276 mg, 1.0 mmol) and K2CO3 (414 mg, 3.0 mmol) in MeOH (20 mL) was heated to reflux for 16 hr. The mixture was filtered and the filtrate was concentrated to give the crude product (280 mg, 58.9%) as a yellow solid. MS (ESI, m/e) [M+1]+ 475.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-378138f3290048b78537a7de3f70afc0
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…