1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67359799, compound

HRID 1667152Notes

Reaction equation

HRID 1667152 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[O:13]=[C:14]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][CH2:16][N:15]1[CH2:32][C:33](O)=[O:34].[F:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][NH:44]2)=[CH:39][CH:38]=1>ClCCl>[F:36][C:37]1[CH:38]=[CH:39][C:40]([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][N:44]2[C:33](=[O:34])[CH2:32][N:15]2[CH2:16][CH2:17][CH2:18][C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]2=[O:13])=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 36861262-(4-fluorophenyl)piperidineHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 67359799HCID 67359799, 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 (Example 68E, 0.050 g, 0.169 mmol) and 2-(4-fluorophenyl)piperidine (0.030 g, 0.169 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF10-4 column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 70% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.46-7.09 (m, 12H), 7.03 (m, 2H), 4.58-4.23 (m, 2H), 3.57 (m, 2H), 2.72-2.55 (m, 2H), 2.45-2.23 (m, 2H), 2.02-1.75 (m, 3H), 1.75-1.47 (m, 6H); MS (DCI+) m/z 471 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a25d48b5732047aaa949b2e7e9562bb6
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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