HCID 522663, compound → HCID 45275805, compound

HRID 1667086Notes

Reaction equation

HRID 1667086 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]([OH:34])=O.[C:35]1([C:41]2([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[O:46][CH2:45][CH2:44][NH:43][CH2:42]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[C:47]1([C:41]2([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[O:46][CH2:45][CH2:44][N:43]([C:32](=[O:34])[CH2:31][N:15]3[CH2:16][CH2:17][C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:14]3=[O:13])[CH2:42]2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 522663HCID 522663, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275805HCID 45275805, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.060 g, 0.313 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.059 g, 0.198 mmol) and 2,2-diphenylmorpholine (0.050 g, 0.209 mmol, CAS 77373-34-3) in dichloromethane (0.5 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 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.43 (s, 20H), 4.15 (s, 2H), 4.09 (s, 2H), 3.39-3.44 (m, 2H), 3.28-3.33 (m, 2H), 3.27 (t, J=6.4 Hz, 2H), 2.57 (t, J=6.6 Hz, 2H); MS (ESI+) m/z 517 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-ca6fe9127f2a4b48914a5da7a33df82f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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