3-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline → HCID 58267967, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][N:7]=[C:6]2[O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].[C:26]([C:30]1[CH:31]=[C:32]([NH:36][C:37](=O)[O:38]C2C=CC=CC=2)[CH:33]=[CH:34][CH:35]=1)([CH3:29])([CH3:28])[CH3:27]>>[C:26]([C:30]1[CH:31]=[C:32]([NH:36][C:37]([NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[C:19]([O:18][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH:20]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)([CH3:29])([CH3:27])[CH3:28]Participants
3
Procedure
The title compound was prepared from 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline from Example 117B (103 mg, 0.3 mmol) and phenyl 3-tert-butylphenylcarbamate from Example 118A (114 mg, 0.42 mmol) using Example 115C. The final product was purified by silica gel column chromatography (25-100% EtOAc/hexanes) to give 1-(3-tert-butylphenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea (74 mg, 0.14 mmol, 48%). 1H NMR (300 MHz, DMSO-d6) δ 8.83 (s, 1H), 8.70 (s, 1H), 8.56 (s, 1H), 7.61-7.58 (m, 2H), 7.49-7.36 (m, 3H), 7.27-7.16 (m, 3H), 7.03 (d, 1H), 6.92 (d, 1H), 4.38-4.32 (m, 2H), 4.00 (s, 3H), 3.81-3.73 (m, 2H), 3.33 (s, 3H), 1.26 (s, 9H); LC-MS (ESI) m/z 517 (M+H)+.
Workup
- customThe final product was purified by silica gel column chromatography (25-100% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-bd9e035508544d1598c84d422e0dfc92
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618289B2
Reaction notes
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