Cesium carbonate → 3-(2-morpholin-4-yl-2-oxoethoxy) 10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 419295Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A glass vial was charged with 4-(bromoacetyl)morpholine (0.05 g, 0.26 mmol, 1.1 eq), 6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-3-ol (0.06 g, 0.23 mmol), DMF (3 mL), and cesium carbonate (0.42 g, 1.3 mmol, 5 eq). The reaction mixture was heated at 90° C. overnight. The reaction was quenched with 30 mL water to provide an off-white precipitate. The solid was collected by vacuum filtration and recrystallized from acetonitrile to provide 0.011 g of 3-(2-morpholin-4-yl-2-oxoethoxy) 10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine, mp 204-206° C.

Workup

customThe reaction was quenched with 30 mL water
customto provide an off-white precipitate
filtrationThe solid was collected by vacuum filtration
customrecrystallized from acetonitrile

Sources & evidence

ORD record: ord-fdc5691575474cf9a0d93fefbbe9af93
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093390B2

Reaction notes

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