Potassium Carbonate → HCID 66906956, compound

HRID 1690496Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-(5-dimethylaminopyridin-2-yl)-2-(4-hydroxy-2-methoxyphenyl) acetamide (0.111 g), 4-chloro-6,7-dimethoxyquinazoline (0.075 g), potassium carbonate (0.2 g) and DMA (2 ml) was stirred and heated to 140° C. in a microwave oven for 20 minutes. The reaction mixture was purified by preparative HPLC using a Waters ‘β Basic Hypersil’ reversed-phase column (5 microns silica, 30 mm diameter, 250 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.137 g); 1H NMR: (CDCl3) 2.92 (s, 6H), 3.75 (s, 2H), 3.91 (s, 3H), 4.07 (s, 3H), 4.08 (s, 3H), 6.86 (s, 1H), 6.88 (m, 1H), 7.10 (m, 1H), 7.33 (s, 1H), 7.41 (d, 1H), 7.55 (s, 1H), 7.73 (d, 1H), 8.09 (d, 1H), 8.16 (br s, 1H), 8.64 (s, 1H); Mass Spectrum: M+H+ 490.

Workup

customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-bd7e4fb506724709998e385de8b13fab
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153643B2

Reaction notes

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