1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 24756696, compound

HRID 1640019Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:17][CH2:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=O.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH:5]=[CH:4][C:3]=1[N:17]1[CH2:18][C:19]2[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:21]1=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-((2-bromo-4-(1-tert-butoxy-1-oxopropan-2-yl)phenylamino)methyl)benzoic acid (4.40 g, 10.1 mmol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (2.13 g, 11.1 mmol) and 4-dimethylaminopyridine (0.617 g, 5.05 mmol) in methylene chloride (80 mL) was stirred at 0° C. and was allowed to warm to room temperature overnight. The mixture was then concentrated and the residue was purified by flash chromatography (silica, 4:1 hexanes/ethyl acetate) to afford tert-butyl 2-(3-bromo-4-(1-oxoisoindolin-2-yl)phenyl)propanoate (3.55 g, 85%) as white foam: 1H NMR (500 MHz, CDCl3) δ 7.96 (d, J=7.6 Hz, 1H), 7.64-7.50 (m, 4H), 7.35 (d, J=1.0 Hz, 2H), 4.79 (s, 2H), 3.63 (q, J=7.2 Hz, 1H), 1.47 (d, J=7.2 Hz, 3H), 1.44 (s, 9H); ESI MS m/z 418 [(M+2)+H]+.

Workup

temperatureto warm to room temperature overnight
concentrationThe mixture was then concentrated
customthe residue was purified by flash chromatography (silica, 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-32a8a4451ed2495c8534444b48df95e3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110681B2

Reaction notes

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