Benzyl 2-formylpyrrolidine-1-carboxylate → HCID 178513714, compound

HRID 2202639Notes

Reaction equation

HRID 2202639 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]([NH2:17])=[O:16].[CH2:18]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH:33]=O)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCO.N1CCCCC1>[C:15]([C:3]1[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[N:5][NH:6][C:2]=1[N:1]=[CH:33][CH:29]1[CH2:30][CH2:31][CH2:32][N:28]1[C:26]([O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27])(=[O:16])[NH2:17]

Participants

5

Reactant 2

HCID 11064320Benzyl 2-formylpyrrolidine-1-carboxylateHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513714HCID 178513714, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide was then suspended in EtOH and benzyl-2-formylpyrrolidine-1-carboxylate (1 eq.) and piperidine (1 drop) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain product as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr.

Workup

  1. temperatureat reflux until intermediate
  2. customAfter reaction
  3. custom(18 hrs) it
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto obtain product as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr

Sources & evidence

ORD record
ord-1c0b0324893c474bbc0f8e9a3d065104
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

Loading…