Diethylenetriamine → HCID 23299879, compound

HRID 1952881Notes

Reaction equation

HRID 1952881 reaction equation
[N-]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:6]1[C:19]2[C:10](=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:20]([OH:22])=O)=[CH:8][CH:7]=1.[NH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][NH2:29]>>[CH:6]1[C:19]2[C:10](=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:20]([NH:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][NH:29][C:20]([C:9]2[C:4]3[C:5](=[CH:16][C:17]4[C:2]([N:3]=3)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:6]=[CH:7][CH:8]=2)=[O:22])=[O:22])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 8111DiethylenetriamineHCID 86755727HCID 86755727, compound

Product 1

HCID 23299879HCID 23299879, compoundYield 84%

Procedure

Reaction of acridine-4-carboxylic acid imidazolide with N,N-bis(2-aminoethyl)amine as above, followed by crystallization of the crude product from MeOH/H2O, gave bis[2-(acridine-4-carboxamido)ethyl]amine (34) (84%). 1H NMR [(CD3)2SO] δ 11.57 (t, J=5.0 Hz, 2 H, 2×CONH), 8.80 (s, 2 H, H-9), 8.46 (d, J=7.1 Hz, 2 H, H-3), 8.08 (d, J=8.4 Hz, 2 H, ArH), 7.92 (d, J=8.7 Hz, 2 H, ArH), 7.79 (d, J=8.1 Hz, 2 H, ArH), 7.55 (t, J=7.7 Hz, 2 H, ArH), 7.41 (t, J=7.6 Hz, 2 H, ArH), 7.27 (t, J=7.4 Hz, 2 H, ArH), 3.73 (q, J=5.5 Hz, 4 H, 2×NHCH2), 3.11 (t, J=5.6 Hz, 4 H, CH2NHCH2). The trihydrochloride salt crystallized from MeOH/EtOAc/HCl, mp 182-184° C. Anal. (C32H27N5O2.3HCl) C, H, N, Cl.

Workup

  1. customfollowed by crystallization of the crude product from MeOH/H2O

Sources & evidence

ORD record
ord-3b6db1c29313489796c40297b76a6ef2
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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