Piperidin-4-ol → 4'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ol
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.OC1CCNC1.[OH:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:37]3[CH2:38][CH2:39][CH:34]([OH:33])[CH2:35][CH2:36]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]Participants
4
Procedure
The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with 4-hydroxypiperidine. A yellow solid 98 was obtained (0.0299 g, 66%). 1H-NMR (CDCl3, 400 MHz) δ 1.76-1.84 (m, 2H), 2.02-2.10 (m, 2H), 3.69-3.76 (m, 2H), 3.83 (s, 3H), 4.01-4.07 (m, 2H), 4.12-4.17 (m, 1H), 6.95 (d, J=6.6 Hz, 1H), 6.99 (s, 1H), 7.01-7.07 (m, 3H), 7.46-7.52 (m, 3H), 7.85 (s, 1H), 8.23 (d, J=6.6 Hz, 1H), MS (APCI) m/z 461 (M+H)+.
Sources & evidence
- ORD record
- ord-81264fc530a1488e9a8363c4ea92a666
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06787542B2
Reaction notes
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