2-Aminopropanol → 6-[6-[(2-hydroxy-1-methyl-ethyl)amino]-pyridin-3-yl]-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

HRID 1670695Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:17]3[N:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=[N:20][C:16]=3[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:25])=[CH:4][CH:3]=1.[NH2:26][CH:27]([CH3:30])[CH2:28][OH:29]>O>[OH:29][CH2:28][CH:27]([NH:26][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:17]3[N:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=[N:20][C:16]=3[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:25])=[CH:4][CH:3]=1)[CH3:30]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of compound 21 (1.0 equiv., 0.583 mmol, 0.228 g) and 2-amino-1-propanol (1.5 ml) was stirred for 50 min under microwave irradiation (microwave settings: temperature=180° C., maximum pressure=17 bar, maximum power=200 W). The reaction mixture was mixed with water (10 ml) and stirred at room temperature for 5 min. The resulting precipitate was filtered off and subsequently washed with water and tetrahydrofuran to afford 6-[6-[(2-hydroxy-1-methyl-ethyl)amino]-pyridin-3-yl]-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (I11) (0.150 g, yield=67%, purity (LC)=96%).

Workup

stirringstirred at room temperature for 5 min
filtrationThe resulting precipitate was filtered off
washsubsequently washed with water and tetrahydrofuran

Sources & evidence

ORD record: ord-bcaa5fab4f704f988a1b3231ecb6fc26
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994187B2

Reaction notes

Loading…