Triethylamine → 6,7-dimethoxy-2-[5-(4-methyl-piperazine-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3H-quinazolin-4-one

HRID 8720Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b, (0.77 g, 3.23 mmol), 5-(4-methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 11a (1.25 g, 3.41 mmol) and triethylamine (0.75 g, 1.04 mL, 7.46 mmol) in DMSO (15 mL) was heated at 80° C. with stirring for 18 h. After cooling to room temperature the reaction was diluted with water. The precipitated white product was collected by filtration, washed with water, and dried to give 0.6 g of 6,7-dimethoxy-2-[5-(4-methyl-piperazine-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-3H-quinazolin-4-one 401, mp. 230–237° C.

Workup

temperatureAfter cooling to room temperature the reaction
filtrationThe precipitated white product was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-9b5833061e994ba492232cab6c831781
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091200B2

Reaction notes

Loading…