3-(Chloromethyl)-5-methyl-1,2-oxazole → N-Methyl-N-(2-{[4-({3-methyl-4-[(5-methylisoxazol-3-yl)methoxy]phenyl}amino) quinazolin-5-yl]oxy}ethyl)acetamide
Reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][CH2:29][N:30]([CH3:34])[C:31](=[O:33])[CH3:32])[N:20]=[CH:19][N:18]=2)=[CH:12][C:11]=1[CH3:35]>>[CH3:34][N:30]([CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:26]=1[C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:2][C:3]3[CH:7]=[C:6]([CH3:8])[O:5][N:4]=3)=[C:11]([CH3:35])[CH:12]=1)=[N:18][CH:19]=[N:20]2)[C:31](=[O:33])[CH3:32]Participants
3
Reactant 2
Product 1
Procedure
The procedure described in Example 3 was repeated using 3-(chloromethyl)-5-methylisoxazole and N-[2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide (obtained as described in Example 75, preparation of starting materials) to give the title compound as a white solid in 14% yield; NMR spectrum (DMSO-d6 373K) 1.95 (s, 3H), 2.23 (s, 3H), 2.43 (s, 3H), 3.57 (s, 3H), 3.88 (t, 2H), 4.47 (m, 2H), 5.15 (s, 2H), 6.29 (s, 1H), 7.05 (d, 1H), 7.15 (d, 1H), 7.34 (d, 1H), 7.48 (d, 1H), 7.54 (dd, 1H), 7.69 (t, 1H), 8.42 (s, 1H), 9.64 (s, 1H); Mass spectrum MH+ 462.
Sources & evidence
- ORD record
- ord-4815d33f27524ba7a8e46b7a608a0562
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625908B2
Reaction notes
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