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

HRID 2183704Notes

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-1a02fd9b6cfd4f12bf4e4557b49327e7
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900220B2

Reaction notes

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