(4-(3-Fluoro-benzyloxy)-3-chlorophenyl)-(6-(2-((2-methanesulphonyl-ethylamino)-methyl)-thiazol-4-yl)quinazolin-4-yl)-amine ditosylate salt → N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine
Reaction equation
BrC1C=C(C=CC=1OCC1C=CC=C(F)C=1)N.S(C1C=CC(C)=CC=1)(O)(=O)=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.[F:40][C:41]1[CH:42]=[C:43]([CH:77]=[CH:78][CH:79]=1)[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([NH:52][C:53]2[C:62]3[C:57](=[CH:58][CH:59]=[C:60]([C:63]4[N:64]=[C:65]([CH2:68][NH:69][CH2:70][CH2:71][S:72]([CH3:75])(=[O:74])=[O:73])[S:66][CH:67]=4)[CH:61]=3)[N:56]=[CH:55][N:54]=2)=[CH:48][C:47]=1[Cl:76]>>[F:40][C:41]1[CH:42]=[C:43]([CH:77]=[CH:78][CH:79]=1)[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([NH:52][C:53]2[C:62]3[C:57](=[CH:58][CH:59]=[C:60]([C:63]4[N:64]=[C:65]([CH2:68][NH:69][CH2:70][CH2:71][S:72]([CH3:75])(=[O:74])=[O:73])[S:66][CH:67]=4)[CH:61]=3)[N:56]=[CH:55][N:54]=2)=[CH:48][C:47]=1[Cl:76]Participants
3
Reactant 2
Product 1
Procedure
The HCL salt of (4-(3-Fluoro-benzyloxy)-3-chlorophenyl)-(6-(2-((2-methanesulphonyl-ethylamino)-methyl)-thiazol-4-yl)quinazolin-4-yl)-amine was prepared according to Procedures 3(a) to (c) and then converted to the (4-(3-Fluoro-benzyloxy)-3-chlorophenyl)-(6-(2-((2-methanesulphonyl-ethylamino)-methyl)-thiazol-4-yl)quinazolin-4-yl)-amine ditosylate salt according to the procedure of Examples 1 and 2. 1H NMR (300 MHz, d6-DMSO) 11.4 (br s, 1H), 9.51 (br s, 1H), 9.24 (s, 1H), 8.95 (s, 1H), 8.68 (d, J=9 Hz, 1H), 8.42 (s, 1H), 7.96 (d, J=9 Hz, 1H), 7.89 (d, J=2 Hz, 1H), 7.64 (dd, J=2, 9 Hz, 1H), 7.47 (m, 5H), 7.34 (m, 3H), 7.20 (t, J=9 Hz, 1H), 7.10 (d, J=8 Hz, 4H), 5.32 (s, 2H), 4.76 (d, 2H), 3.61 (s, 4H), 3.15 (s, 3H), 2.28 (s, 6H).
Sources & evidence
- ORD record
- ord-76d2364698b34823b4463a12d9d1a4dd
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141576B2
Reaction notes
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