1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67443249, compound

HRID 1667211Notes

Reaction equation

HRID 1667211 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.[O:35]1[CH:39]=[CH:38][N:37]=[C:36]1[CH2:40][NH2:41]>ClCCl>[O:35]1[CH:39]=[CH:38][N:37]=[C:36]1[CH2:40][NH:41][C:32](=[O:34])[CH2:31][N:15]1[CH2:16][CH2:17][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)[C:14]1=[O:13]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18947655Oxazol-2-ylmethanamineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 67443249HCID 67443249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 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 (0.050 g, 0.169 mmol; Example 1C) and oxazol-2-ylmethanamine (0.018 g, 0.186 mmol) were stirred together in dichloromethane (0.5 mL) at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 (Analogix®) column and the product eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (Flow=30 mL/minute) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.58 (s, 1H), 7.38-7.19 (m, 10H), 7.05 (s, 1H), 6.68 (s, 1H), 4.48 (d, J=5.6, 2H), 4.08 (s, 2H), 3.53 (t, J=6.5, 2H), 2.83 (t, J=6.5, 2H); MS (ESI+) m/z 376.0 (M+H)+.

Workup

  1. washthe product eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-006429ec1d874577b2fe430434100c9c
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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