N,N'-Bis(3-aminopropyl)ethylenediamine → HCID 86664385, compound

HRID 1056926Notes

Reaction equation

HRID 1056926 reaction equation
NCCCN[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH2:11]N.C1C2[C:19]3[C:30](=O)[C:29]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:20]=3OC(=O)C=2C=CC=1>C(Cl)(Cl)Cl>[CH:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:20]=[C:19]1[C:24]3=[C:20]4[C:27](=[CH:26][C:25]3=[C:6]3[C:11]([CH:10]=[CH:9][N:8]=[CH:7]3)=[C:30]12)[CH:28]=[CH:29][CH:30]=[CH:19]4

Participants

4

Reactant 2

HCID 25378N,N'-Bis(3-aminopropyl)ethylenediamineHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 86664385HCID 86664385, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bis-1,2-{(5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline)-(6-propyl-tert-BOCamino)}ethane (13b), N,N′-Bis(3-aminopropyl)-1,2-ethanediamine (11h) (0.16 g, 0.85 mmol) was added to a stirred solution of indenobenzopyran 4d (0.46 g, 1.87 mmol) in CHCl3 (150 mL) and the reaction mixture was stirred under reflux for 72 h, providing bisindenoisoquinoline 12 h as a crude intermediate. Upon allowing the reaction mixture to cool to room temperature, Et3N (0.6 mL, 4.24 mmol) and Boc2O (0.56 g, 2.60 mmol) were added to the reaction mixture and the mixture was allowed to stir at room temperature for 8 h. The crude reaction mixture was purified by flash column chromatography (SiO2/20% EtOAc in hexane, then 1-5% MeOH in CHCl3) to provide Boc-protected bisindenoisoquinoline 13b (550 mg, 76%) as an orange solid: mp 106-108° C. 1HNMR (CDCl3) δ 8.60 (bs, 2H), 8.23 (bs, 2H), 7.65 (bs, 2H), 7.55 (d, J=6.7 Hz, 2H), 7.40-7.32 (m, 8H), 4.48 (bs, 4H), 3.45 (bs, 8H), 2.12 (bs, 4H), 1.44 (s, 9H), 1.39 (s, 9H); ESIMS m/z (rel intensity) 835 (MH+, 22), 735 (MH+-Boc, 100). Anal. Calcd for C50H50N4O8.0.3H2O: C, 71.46; H, 6.07; N, 6.67. Found: C, 71.15; H, 6.19; N, 6.61.

Workup

  1. temperatureunder reflux for 72 h

Sources & evidence

ORD record
ord-3861a11b6e2247008b14e30807c7fb90
Source dataset
uspto-grants-2016_07
Patent number
US09399660B2

Reaction notes

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