Phenyl 5-methylisoxazol-3-ylcarbamate → 1-(3-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-methylisoxazol-3-yl)urea

HRID 871444Notes

Reaction equation

HRID 871444 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].[CH3:23][C:24]1[O:28][N:27]=[C:26]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[CH:25]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]([NH:19][C:30]([NH:29][C:26]2[CH:25]=[C:24]([CH3:23])[O:28][N:27]=2)=[O:31])[CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 4519264Phenyl 5-methylisoxazol-3-ylcarbamateHCID 498410023-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 569537371-(3-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-methylisoxazol-3-yl)ureaYield 25%

Procedure

3-(6,7-dimethoxyquinazolin-4-yloxy)aniline from Example 113A (89 mg, 0.3 mmol) and phenyl 5-methylisoxazol-3-ylcarbamate from the previous step (98 mg, 0.42 mmol) were reacted using Example 115C to give 1-(3-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-methylisoxazol-3-yl)urea (31 mg, 0.074 mmol, 25%). 1H NMR (300 MHz, DMSO-d6) δ 9.53 (s, 1H), 9.01 (s, 1H), 8.56 (s, 1H), 7.57 (s, 1H), 7.55 (s, 1H), 7.45-7.35 (m, 2H), 7.26 (d, 1H), 6.97 (d, 1H), 6.51 (s, 1H), 3.99 (s, 6H), 2.35 (s, 3H); LC-MS (ESI) m/z 422 (M+H)+.

Sources & evidence

ORD record
ord-6c244a0545664123824659719817ae93
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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