Pyrrolidine → methyl 1-methyl-3-oxo-2-phenyl-5-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1H-pyrazole-4-carboxylate

HRID 415885Notes

Reaction equation

HRID 415885 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[C:4]=1[C:16]([O:18][CH3:19])=[O:17].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCl>[CH3:8][N:7]1[C:3]([CH2:2][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:5](=[O:15])[N:6]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 31268Pyrrolidine2×HCID 59598414methyl 5-(bromomethyl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate

Product 1

HCID 59598366methyl 1-methyl-3-oxo-2-phenyl-5-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1H-pyrazole-4-carboxylateYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 5-(bromomethyl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (1.266 g, 3.9 mmol) was dissolved in dichlormethane (30 ml) and pyrrolidine (0.40 ml, 4.8 mmol) was added via syringe. The reaction was stirred under nitrogen at room temperature. After about 20 minutes, more pyrrolidine (0.090 ml, 1.1 mmol) was added, and stirring was continued for 3.5 hours. The reaction was concentrated and purified on silica gel (dichlormethane, MeOH, 2 N ammonia in MeOH) to give the desired methyl 1-methyl-3-oxo-2-phenyl-5-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1H-pyrazole-4-carboxylate (1.182 g, 70% purity by HPLC, 2.62 mmol, 67% yield). MS (ESI pos. ion) m/z: 316 (MH+). Calc'd exact mass for C17H21N3O3: 315.

Workup

  1. stirringstirring
  2. waitwas continued for 3.5 hours
  3. concentrationThe reaction was concentrated
  4. custompurified on silica gel (dichlormethane, MeOH, 2 N ammonia in MeOH)

Sources & evidence

ORD record
ord-cd9295e65a8549c38cc414ba60061528
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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