1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-{[6-(trifluoromethyl)pyridin-3-yl]methyl}acetamide

HRID 1667064Notes

Reaction equation

HRID 1667064 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].[F:35][C:36]([F:46])([F:45])[C:37]1[N:42]=[CH:41][C:40]([CH2:43][NH2:44])=[CH:39][CH:38]=1>ClCCl>[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:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:17][CH2:16][N:15]1[CH2:31][C:32]([NH:44][CH2:43][C:40]1[CH:41]=[N:42][C:37]([C:36]([F:46])([F:35])[F:45])=[CH:38][CH:39]=1)=[O:33]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 452755962-(2-oxo-3,3-diphenylpyrrolidin-1-yl)-N-{[6-(trifluoromethyl)pyridin-3-yl]methyl}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 (6-(trifluoromethyl)pyridin-3-yl)methanamine (0.033 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 SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.48 (s, 1H), 7.53-7.61 (m, 2H), 7.22-7.30 (m, 10H), 6.50-6.56 (m, 1H), 4.32 (d, J=6.1 Hz, 2H), 4.06 (s, 2H), 3.51 (t, J=6.4 Hz, 2H), 2.81 (t, J=6.4 Hz, 2H); MS (ESI−) m/z 452 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-458b926370db4946b394ae0cd96fc86e
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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