1-(1-Isocyanatoethyl)naphthalene → 1-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]-3-[1-(1-naphthyl)ethyl]urea
Reaction equation
[C:1]1([CH:11]([N:13]=[C:14]=[O:15])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH2:30][CH:31]1[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1)[N:20]=[CH:19][N:18]=[C:17]2[NH:16][C:14]([NH:13][CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:12])=[O:15]Participants
3
Procedure
Using an analogous procedure to that described in Example 14, 1-(1-naphthyl)ethyl isocyanate was reacted with 4-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline to give the title compound; NMR Spectrum: (CDCl3) 1.41-1.57 (m, 2H), 1.76 (m, partially obscured by water peak), 1.86-2.05 (m, 5H), 2.02 (s, 3H), 2.91 (s, 2H), 3.87 (s, 3H), 4.02 (d, 2H), 5.95 (s, 1H), 7.19 (s, 1H), 7.23 (s, 1H), 7.39-7.52 (m, 3H), 7.6 (d, 1H), 7.71 (d, 1H), 7.84 (m, 1H), 8.12 (m, 1H), 8.57 (s, 1H), 8.64 (s, 1H), 10.67 (t, 1H); Mass Spectrum: M+H+ 500.
Sources & evidence
- ORD record
- ord-35e1bb0a7bcd4c4cbf0661303e38c360
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06806274B1
Reaction notes
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