Pyrrolidine → 5-(4-Methylphenyl)-4-(pyrrolidin-1-ylcarbonyl)isoxazole

HRID 1446317Notes

Reaction equation

HRID 1446317 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 248099225-(4-Methylphenyl)-4-(pyrrolidin-1-ylcarbonyl)isoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (30 mg, 0.14 mmol) in dichloromethane (1 mL) was added pyrrolidine (11 mg, 0.16 mmol, 1.1 eq.), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C15H16N2O2: 256.1212, found 256.1214.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-81182cda54bd42fbbbb87109ae75ad48
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

Loading…