Morpholine → HCID 22648014, compound

HRID 394219Notes

Reaction equation

Br[CH2:2][C:3]([NH:5][C:6]([C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][NH:14][C:15](=[O:27])[N:16]2[C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])=[C:11]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[CH:10]=1)([CH3:8])[CH3:7])=[O:4].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:11]1[CH:10]=[C:9]([C:6]([NH:5][C:3](=[O:4])[CH2:2][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)([CH3:8])[CH3:7])[CH:18]=[C:17]2[C:12]=1[CH2:13][NH:14][C:15](=[O:27])[N:16]2[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-bromo-N-{1-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methylethyl}acetamide (30 mg, 0.05 mmol, 1 eq) in DMF (0.5 mL) was added morpholine (0.01 mL) and diisopropylethylamine (0.02 mL). The mixture was warmed to and maintained at 80° C. for 1.5 h at which time HPLC analysis indicated complete reaction. The mixture was diluted with ethyl acetate and washed 3× with dilute NaOH. The organic extract was dried over anhydrous Na2SO4, filtered and concentrated giving N-{1-[5-(2-chlorophenyl)-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methylethyl}-2-morpholin-4-ylacetamide. Mass spectrum 587.2 (M+1); 589.2 (M+3).

Workup

temperatureThe mixture was warmed to and
customreaction
washwashed 3× with dilute NaOH
extractionThe organic extract
dry with materialwas dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-75a36b3db87e4cb1acf1eaa14ab4b48a
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

Loading…