1-Propanesulfonyl chloride → 2-[4-[7-fluoro-5-(1-propylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]-5-propylpyrimidine
Reaction equation
[F:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]4[N:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][N:18]=4)[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[C:4]([C:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=2)[CH:3]=1.[CH2:32]([S:35](Cl)(=[O:37])=[O:36])[CH2:33][CH3:34]>>[F:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]4[N:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][N:18]=4)[CH2:15][CH2:16]3)[CH2:7][C:6]=2[CH:5]=[C:4]([C:26]2[CH2:27][CH2:28][N:29]([S:35]([CH2:32][CH2:33][CH3:34])(=[O:37])=[O:36])[CH2:30][CH:31]=2)[CH:3]=1Participants
Reactant 2
Product 1
Procedure
Example 5 was prepared from Compound 3H and propane-1-sulfonyl chloride in a similar manner to the procedure described in Example 1. 1H NMR (500 MHz, CDCl3) δ ppm 8.15 (s, 2 H), 6.95 (s, 1 H), 6.92 (d, J=12.1 Hz, 1 H), 5.94 (ddd, J=3.4, 1.9, 1.8 Hz, 1 H), 4.76-4.87 (m, 2 H), 4.63-4.73 (m, 1 H), 3.97 (q, J=2.8 Hz, 2 H), 3.53 (t, J=5.6 Hz, 2 H), 3.24 (dd, J=15.7, 9.1 Hz, 1 H), 3.04 (dd, J=15.7, 8.3 Hz, 1 H), 2.91-2.98 (m, 2 H), 2.78-2.89 (m, J=12.9, 12.9, 6.1, 2.8 Hz, 2 H), 2.52-2.59 (m, 2 H), 2.39 (t, J=7.4 Hz, 2 H), 2.05 (d, J=13.2 Hz, 1 H), 1.97 (dddd, J=11.4, 7.9, 7.7, 3.6 Hz, 1 H), 1.82-1.91 (m, 2 H), 1.75 (d, J=12.9 Hz, 1 H), 1.57 (sxt, J=7.4 Hz, 2 H), 1.39 (qd, J=12.4, 4.3 Hz, 2 H), 1.07 (t, J=7.4 Hz, 3 H), 0.93 (t, J=7.4 Hz, 3 H).
Sources & evidence
- ORD record
- ord-17424995e1b14b95a078016444e7a2b3
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729084B2
Reaction notes
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