Cyanogen Bromide → HCID 178508340, compound

HRID 1972221Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N:29]#[C:30]Br>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=4)[CH2:15][NH:16][C:30]3=[NH:29])=[CH:9][CH:8]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N1-(4-(4-chlorophenoxy)phenyl)-1-(3-(trifluoromethyl)phenyl)ethane-1,2-diamine (20.0 mg, 0.0492 mmol) in EtOH (0.5 mL) are added cyanogen bromide (6.2 mg, 0.0590 mmol) and TEA (8.22 μL, 0.0590 mmol). The reaction mixture is heated at 80° C. for 2 h before removal of the solvent. The residue is purified by preparatory LC/MS to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 7.65-7.50 (m, 4H), 7.33 (d, 2H), 7.01 (d, 2H), 6.94 (m, 4H), 5.24 (dd, 1H), 4.30 (t, 1H), 3.79 (dd, 1H); HPLC-MS calculated for C22H17ClF3N3O (M+H+) 432.1, found 432.1.

Workup

customThe residue is purified by preparatory LC/MS

Sources & evidence

ORD record: ord-118102e54f6e4b2ba3305a298e4794f1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

Loading…