2-Fluoroethyl methanesulfonate → 1-Cyclopropyl-3-(3-fluoro-4-(2-(5-((4-((2-fluoroethyl)(methyl)amino)piperidin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea
Reaction equation
CS(O[CH2:6][CH2:7][F:8])(=O)=O.[CH:9]1([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]4[CH:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([CH2:38][N:39]6[CH2:44][CH2:43]N(CCF)C[CH2:40]6)=[CH:34][N:33]=5)[S:31][C:24]=34)=[C:18]([F:48])[CH:17]=2)=[O:14])[CH2:11][CH2:10]1>>[CH:9]1([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]4[CH:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([CH2:38][N:39]6[CH2:44][CH2:43][CH:9]([N:12]([CH2:6][CH2:7][F:8])[CH3:13])[CH2:10][CH2:40]6)=[CH:34][N:33]=5)[S:31][C:24]=34)=[C:18]([F:48])[CH:17]=2)=[O:14])[CH2:11][CH2:10]1Participants
3
Reactant 2
Product 1
Procedure
Compound 421 (example 269) was prepared in one step by reacting the amine precursor 401 (table 31) with compound 419, similarly to compound 420 (example 268, scheme 77). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.73 (s, 1H), 8.54 (d, J=1.6 Hz, 1H), 8.52 (d, J=5.6 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.85 (dd, J=8.0, 2.0 Hz, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.22-7.18 (m, 1H), 6.64 (d, J=5.2 Hz, 1H), 6.56 (bd, J=2.8 Hz, 1H), 4.51 (t, J=5.2 Hz, 1H), 4.39 (t, J=5.2 Hz, 1H), 3.54 (s, 2H), 2.90-2.82 (m, 2H), 2.77-2.63 (m, 2H), 2.59-2.50 (m, 1H), 2.40-2.30 (m, 1H), 2.22 (s, 3H), 2.02-1.91 (m, 2H), 1.69-1.61 (m, 2H), 1.50-1.38 (m, 2H), 0.68-0.62 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 593.59 (M+H).
Sources & evidence
- ORD record
- ord-57262cd041694e76bc1c694bf19d08f9
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906852B2
Reaction notes
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