3-Chloro-1-benzofuran-7-amine → 4-(3-Chlorobenzofuran-7-ylamino)-7-(2-pyrrolidin-1-ylethoxy)-5-cyclopentyloxyquinazoline dihydrochloride
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:9][C:10]=2[O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:5]=[CH:4][N:3]=1.[NH2:26][C:27]1[C:35]2[O:34][CH:33]=[C:32]([Cl:36])[C:31]=2[CH:30]=[CH:29][CH:28]=1>>[ClH:1].[ClH:36].[Cl:36][C:32]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:26][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:18][CH2:19][CH2:20][N:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)=[CH:9][C:10]=4[O:12][CH:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)[N:5]=[CH:4][N:3]=3)[C:35]=2[O:34][CH:33]=1Participants
3
Procedure
Using an analogous procedure to that described in Example 47, 4-chloro-5-cyclopentyloxy-7-(2-pyrrolidin-1-ylethoxy)quinazoline (0.1 g) was reacted with 7-amino-3-chlorobenzofuran (0.051 g) to give the title compound, as a dihydrochloride salt (0.074 g), a portion of which was converted into the free base using an analogous procedure to that described in Example 3. The free base gave the following characterising data: NMR Spectrum: (CDCl3) 1.7-1.8 (m, 2H), 1.8-2.0 (m, 6H), 2.1-2.3 (m, 4H), 2.7 (br s, 4H), 3.02 (m, 2H), 4.3 (t, 2H), 5.08 (m, 1H), 6.61 (d, 1H), 6.84 (d, 1H), 7.3-7.45 (m, 2H), 7.65 (s, 1H), 8.64 (s, 1H), 8.76 (d, 1H), 10.3 (s, 1H); Mass Spectrum: M+H+ 493 and 495.
Sources & evidence
- ORD record
- ord-b871266fcc5241b6992aa6d74164c017
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696214B2
Reaction notes
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