7-(Benzyloxy)-4-chloro-6-methoxyquinazoline → HCID 69935072, compound

HRID 536070Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1>CC(O)C>[CH3:18][NH:17][S:14]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([F:11])([F:13])[F:12])=[C:2]([NH:1][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH:3]=1)(=[O:15])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-amino-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (3.0 g, 10.7 mmol) in i-PrOH (100 mL) was treated with 4-chloro-6-(methyloxy)-7-[(phenylmethyl)oxy]quinazoline (3.2 g, 10.7 mmol, prepared according to J. Med. Chem. (1999) 42 5369) and stirred at 80° C. for 2 hours before being concentrated. The residue was washed with petroleum ether and dried to give N-methyl-3-({6-(methyloxy)-7-[(phenylmethyl)oxy]-4-quinazolinyl}amino)-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (4.2 g, 72%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.42 (br. s., 1 H), 8.75 (s, 1 H), 8.20 (s, 1 H), 7.80-7.84 (m, 2 H), 7.49-7.57 (m, 4 H), 7.35-7.49 (m, 4 H), 5.34 (s, 2 H), 4.91 (q, J=8.82 Hz, 2 H), 3.99 (s, 3 H), 2.45 (d, J=5.07 Hz, 3 H). MS (m/z) 549.1 (M+H+).

Workup

concentrationbefore being concentrated
washThe residue was washed with petroleum ether
customdried

Sources & evidence

ORD record: ord-3d344a26476149d2b9d6e73979fb5a64
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859571B2

Reaction notes

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