1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59202064, compound

HRID 1626060Notes

Reaction equation

HRID 1626060 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.[CH2:22]([N:24]([CH2:30][CH3:31])[C:25](=[O:29])[C@@H:26](O)[CH3:27])[CH3:23]>ClCCl.CN(C1C=CN=CC=1)C>[C:7]([O:9][C@H:26]([C:25](=[O:29])[N:24]([CH2:30][CH3:31])[CH2:22][CH3:23])[CH3:27])(=[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 86639355HCID 86639355, compound

Product 1

HCID 59202064HCID 59202064, compoundYield 21.5%

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 12 mL of dichloromethane (DCM) at ca. 0° C. (2S)—N,N-Diethyl-2-hydroxypropanamide (0.44 g, 3.07 mmol) (0.44 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 mass-guided preparative HPLC/lyophilization and by silica gel flash column chromatography (Biotage) using ethyl acetate (EtOAc) and hexanes afforded 0.17 g (18% yield) of the title compound (33) as a clear oil. 1H NMR (CDCl3, 400 MHz): δ 6.95-6.87 (m, 2H), 5.43 (q, J=6.8 Hz, 1H) 3.80 (s, 3H), 3.50-3.26 (m, 4H), 1.49 (d, J=6.4 Hz, 3H), 1.26 (t, J=6.8, 3H), 1.12 (t, J=7.6 Hz, 3H). MS (ESI): m/z 258.06 (M+H)+.

Workup

  1. customAfter work-up and isolation, and purification by mass-guided preparative HPLC/lyophilization

Sources & evidence

ORD record
ord-43eb36a31bfd485c85ba09f0c7d6e803
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

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