HCID 136983798, compound → 2-Oxo-6-(4-phenoxyphenyl)-1,2-dihydrospiro[imidazo[1,2-b]pyrazole-3,4'-piperidine]-7-carboxamide

HRID 64356Notes

Reaction equation

HRID 64356 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([N:17]3[N:18]=[C:19]([C:24]4[CH:29]=[CH:28][C:27]([O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:26][CH:25]=4)[C:20]([C:21]([NH2:23])=[O:22])=[C:16]3[NH:15][C:14]2=[O:37])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[O:37]=[C:14]1[C:11]2([CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:17]2[N:18]=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)[C:20]([C:21]([NH2:23])=[O:22])=[C:16]2[NH:15]1

Participants

4

Reactant 1

HCID 136983798HCID 136983798, compound

Product 1

HCID 1369281092-Oxo-6-(4-phenoxyphenyl)-1,2-dihydrospiro[imidazo[1,2-b]pyrazole-3,4'-piperidine]-7-carboxamideYield 289.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1′-benzyl-2-oxo-6-(4-phenoxyphenyl)-1,2-dihydrospiro[imidazo[1,2-b]pyrazole-3,4′-piperidine]-7-carboxamide (120 mg, 0.24 mmol) in MeOH (10 mL) was added 10% w/w Pd(OH)2/C (5 mg) and stirred for 16 hr under H2. 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]+ 403.9.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a09d7eda16a147f98f1fd857dc63a4de
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…