Ethylenediamine → HCID 24752057, compound

HRID 553409Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].[F:5][C:6]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:7]=1[C:8](Cl)=O.[C:17](#[N:19])C>>[F:5][C:6]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:7]=1[CH2:8][N:3]1[CH2:2][CH2:1][N:4]([CH2:8][C:7]2[CH:11]=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:6]=2[F:5])[C:17]1=[NH:19]

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 6342Acetonitrile

HCID 1451642,4,5-Trifluorobenzoyl chloride

Product 1

HCID 24752057HCID 24752057, compound

Procedure

The title compound was prepared in three steps as described in Procedure D. In the first step, ethylenediamine was reacted in acetonitrile with 2,4,5-trifluorobenzoylchloride (2 eq) in the presence of TEA to give the N,N′-dibenzoylated ethylenediamine upon aqueous work-up. After the last step (reaction with cyanogen bromide, performed at 200° C. for 60 min using MW heating), the precipitated solid was filtered off and recrystallized to give the title compound as the hydrogen bromide salt. MS (ES+) m/z 374 ([M+1]+, 100); HR-MS: 374.1086 ([M+1]+, C17H14F6N3; calc. 374.10919).

Sources & evidence

ORD record: ord-59f9ba7eac6147c1bcf39b005c2b4c53
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048877B2

Reaction notes

Loading…