1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59202054, compound

HRID 1624178Notes

Reaction equation

HRID 1624178 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]([OH:9])=[O:8])=[O:4].Cl.CN(C)CCCN=C=NCC.O[C@@H:23]([CH3:35])[C:24]([N:26]([CH2:31][CH2:32][O:33][CH3:34])[CH2:27][CH2:28][O:29][CH3:30])=[O:25]>ClCCl.CN(C1C=CN=CC=1)C>[C:7]([O:9][C@H:23]([C:24](=[O:25])[N:26]([CH2:27][CH2:28][O:29][CH3:30])[CH2:31][CH2:32][O:33][CH3:34])[CH3:35])(=[O:8])/[CH:6]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5369209Monomethyl FumarateHCID 86639354HCID 86639354, compound

Product 1

HCID 59202054HCID 59202054, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Following general procedure B2, (2E)-3-(methoxycarbonyl)prop-2-enoic acid (methyl hydrogen fumarate, MHF) (0.50 g, 3.84 mmol) was activated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) (0.88 g, 4.60 mmol) in 20 mL of dichloromethane (DCM) at ca. 0° C. (2S)-2-Hydroxy-N,N-bis(2-methoxyethyl)propanamide (0.63 g, 3.07 mmol) and 4-(N,N-dimethyl)aminopyridine (DMAP) (0.40 g, 3.18 mmol) were added to the activated carboxylic acid. After work-up and isolation, and purification by silica gel flash column chromatography (Biotage) using ethyl acetate (EtOAc) and hexanes (2:1) afforded 0.16 g (14% yield) of the title compound (32) as a clear oil. 1H NMR (CDCl3, 400 MHz): δ 6.93-6.77 (m, 2H), 5.53 (q, J=6.4 Hz, 1H), 3.80 (s, 3H), 3.58-3.50 (m, 8H), 3.47-3.32 (2s, 6H), 1.49 (d, J=6.8 Hz, 3H). MS (ESI): m/z 318.05 (M+H)+.

Workup

  1. customAfter work-up and isolation, and purification by silica gel flash column chromatography (Biotage)

Sources & evidence

ORD record
ord-078117fbc729499594f6dd997a10b524
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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