(2H-1,3-benzodioxol-5-yl)boronic acid → N1,N1'-((5-(benzo[d][1,3]dioxol-5-yl)-1,3-phenylene)bis(methylene))bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chloride

Participants

Role	Name	HCID	Charge
Reactant	(2H-1,3-benzodioxol-5-yl)boronic acid	HCID 2734371	—
Reactant	1,1-Dimethylethyl N-(3-((3-aminopropyl)amino)propyl)carbamate	HCID 2786632	—
Reactant	5-Bromobenzene-1,3-dicarbaldehyde	HCID 14383230	—
Reactant	N1,N1'-((5-(benzo[d][1,3]dioxol-5-yl)-1,3-phenylene)bis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine), hydrochloride salt	HCID 131737044	—
Product	N1,N1'-((5-(benzo[d][1,3]dioxol-5-yl)-1,3-phenylene)bis(methylene))bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chloride	HCID 131737043	—

Reaction Steps

Example 46 was prepared in a similar fashion to Example 45 (CZ-58) from 5-bromoisophthaldehyde, benzo[d][1,3]dioxol-5-ylboronic acid, and tert-butyl (3-((3-aminopropyl)amino)propyl)carbamate. N1,N1′-((5-(benzo[d][1,3]dioxol-5-yl)-1,3-phenylene)bis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine), hydrochloride salt: 1H NMR (500 MHz, D2O) δ 7.72 (s, 2H), 7.49 (s, 1H), 7.15 (s, 2H), 6.93 (d, J=8.5 Hz, 1H), 5.95 (s, 2H), 4.30 (s, 4H), 3.21-3.12 (m, 8H), 3.05 (t, J=8.0 Hz, 4H), 2.17-2.02 (m, 8H). 13C NMR (125 MHz, D2O) δ 148.1, 147.6, 142.3, 133.3, 132.2, 130.8, 129.7, 129.6, 129.4, 121.1, 109.0, 107.5, 101.6, 51.0, 44.8, 44.8, 44.4, 36.6, 23.9, 22.8.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09439433B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-d251a2747cdb4a3495a4c7a50dbe7f60
Source note	uspto-grants-2016_09