2-Chloroethyl isocyanate → N'-(2-Chloroethyl)-N-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methylurea
Reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[Cl:7][C:8]1[CH:9]=[C:10]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:33][CH2:34][CH2:35][NH:36][CH3:37])[N:26]=[CH:25][N:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>>[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[N:36]([CH2:35][CH2:34][O:33][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:32]=1[C:23]([NH:22][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[C:8]([Cl:7])[CH:9]=1)=[N:24][CH:25]=[N:26]2)[CH3:37]Participants
3
Procedure
The procedure described in Example 120 was repeated using 2-chloroethyl isocyanate and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials) to give the title compound as a solid in 80% yield; NMR spectrum (DMSO-d6 @ 373K) 2.90 (s, 3H), 3.15-3.25 (q, 2H), 3.43-3.50 (t, 2H), 3.75-3.85 (t, 2H), 4.35-4,45 (t, 2H), 5.25, 6.35 (bs, 1H), 7.08-7.13 (d, 1H), 7.13-7.30 (m, 1H), 7.35-7.40 (m, 2H), 7.50-7.65 (m, 2H), 7.65-7.80 (m, 1H), 7.80-7.90 (t, 1H), 7.95 (d, 1H), 8.50 (s, 1H), 8.55-8.60 (d, 1H), 9.80 (s, 1H); Mass spectrum MH+ 541.3.
Sources & evidence
- ORD record
- ord-42497cdf58c94930870a231044d5a2c3
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625908B2
Reaction notes
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