Brimonidine → N-(4,5-dihydro-1H-imidazol-2-yl)-5-methylquinoxalin-6-amine

HRID 1941132Notes

Reaction equation

Br[C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[CH3:18][Sn](C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH3:18][C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 145 °C

Procedure

A sealable reaction tube was charged with 5-bromo-6-(2-imidazolin-2-ylamino) quinoxaline (104 mg., 0.36 mmol) (prepared as noted above), tetramethyl tin (214 mg., 1.2 mmol) and (Ph3P)2PdCl2 (10 mg) and dry dimethylformamide (2 ml) in a reaction tube. The reaction mixture was purged with dry nitrogen gas. The tube was sealed and heated to 145° C. for 6 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuou The dark brown residue was chromatographed (SiO2 ; 5/1 CHCl3 /CH3OH saturated with NH3 (g)) to yield 46.5 mg (53%) of the title compound as a light yellow solid. An analytical sample was prepared by recrystallization from CHCl3 /CH3OH and had a melting point of 183°-186° C. The title compound was characterized by 1H and 13CNMR, IR and mass spectral analysis.

Workup

customThe reaction mixture was purged with dry nitrogen gas
customThe tube was sealed
temperatureThe reaction mixture was cooled to room temperature
customthe solvent removed in vacuou The dark brown residue
customwas chromatographed (SiO2 ; 5/1 CHCl3 /CH3OH saturated with NH3 (g))

Sources & evidence

ORD record: ord-d252567254244441b2e28f576d831a81
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703077

Reaction notes

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