1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[(1-methyl-1H-pyrazol-3-yl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

HRID 1667066Notes

Reaction equation

HRID 1667066 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[O:13]=[C:14]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]1[CH2:31][C:32](O)=[O:33].[CH3:35][N:36]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[N:37]1>ClCCl>[CH3:35][N:36]1[CH:40]=[CH:39][C:38]([CH2:41][NH:42][C:32](=[O:33])[CH2:31][N:15]2[CH2:16][CH2:17][C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:14]2=[O:13])=[N:37]1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275490N-[(1-methyl-1H-pyrazol-3-yl)methyl]-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and (1-methyl-1H-pyrazol-3-yl)methanamine (0.021 g, 0.186 mmol) were combined and stirred together in dichloromethane (0.5 mL) at room temperature. After stirring overnight, the reaction was loaded directly onto a SF10-8 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 0.4% to 7.5% methanol/dichloromethane over 20 minutes (flow=20 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.23-7.34 (m, 11H), 6.40 (t, J=6.0 Hz, 1H), 6.06 (d, J=2.2 Hz, 1H), 4.38 (d, J=5.3 Hz, 2H), 4.05 (s, 2H), 3.82 (s, 3H), 3.50 (t, J=6.4 Hz, 2H), 2.82 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 387 (M−H)−.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-b84fa5cb4a9144eebac94f35ba50a122
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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