1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-{2-[4-(5-Chloropyridin-2-yl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

HRID 1667113Notes

Reaction equation

HRID 1667113 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[O:14]=[C:15]1[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][N:16]1[CH2:32][C:33](O)=[O:34].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:33](=[O:34])[CH2:32][N:16]3[CH2:17][CH2:18][C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:15]3=[O:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 38053011-(5-Chloropyridin-2-yl)piperazineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 673582131-{2-[4-(5-Chloropyridin-2-yl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(5-chloropyridin-2-yl)piperazine (0.037 g, 0.186 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol) in dichloromethane (2 mL) was stirred 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 25 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.12 (dd, J=2.6, 0.7 Hz, 1H), 7.45 (dd, J=9.0, 2.7 Hz, 1H), 7.18-7.38 (m, 10H), 6.54 (dd, J=9.1, 0.7 Hz, 1H), 4.24 (s, 2H), 3.67-3.72 (m, 2H), 3.54 (t, J=6.6 Hz, 2H), 3.51-3.56 (m, 2H), 3.44-3.50 (m, 2H), 3.36-3.42 (m, 2H), 2.82 (t, J=6.6 Hz, 2H); MS (ESI+) m/z 475 (M+H)+.

Workup

  1. washthe title compound was eluted
  2. customover 25 minutes

Sources & evidence

ORD record
ord-56472b24ab2349dba86d24f0d3a1edc3
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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