2,2-Dimethyl-1,3-dioxan-5-ol → HCID 68578103, compound
Reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].[CH3:28][C:29]1([CH3:36])[O:34][CH2:33][CH:32](O)[CH2:31][O:30]1>>[CH3:28][C:29]1([CH3:36])[O:34][CH2:33][CH:32]([O:22][C:18]2[C:19]([CH3:21])=[CH:20][C:15]([C:12]3[N:11]=[C:10]([C:8]4[CH:7]=[C:6]([CH3:25])[N:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:26][CH3:27])[CH:9]=4)[O:14][N:13]=3)=[CH:16][C:17]=2[CH2:23][CH3:24])[CH2:31][O:30]1Participants
Procedure
4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (100 mg, 0.273 mmol, Example 12) is reacted with 2,2-dimethyl-[1,3]dioxan-5-ol (54 mg, 0.409 mmol) under Mitsunobu conditions as described in Example 18, step a) to give (4-{3-[4-(2,2-dimethyl-[1,3]dioxan-5-yloxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-6-methyl-pyridin-2-yl)-diethyl-amine (65 mg) as yellow oil; LC-MS: tR=0.97 min; [M+1]+=481.27. This material (65 mg, 0.135 mmol) is dissolved in 25% aq. HCl (3 mL) and the resulting mixture is stirred at rt for 2 h. The solvent is evaporated and the crude product is purified by prep. HPLC to give the title compound (23 mg) as yellow solid; LC-MS: tR=0.80 min; [M+1]+=441.24; 1H NMR (CD3OD): δ 1.22 (t, J=7.0 Hz, 6H), 1.28 (t, J=7.5 Hz, 3H), 2.41 (s, 3H), 2.44 (s, 3H), 2.82 (q, J=7.5 Hz, 2H), 3.61 (q, J=7.0 Hz, 4H), 3.78 (dd, J=11.3, 4.8 Hz, 2H), 3.84 (dd, J=11.5, 5.0 Hz, 2H), 4.11-4.18 (m, 1H), 7.02 (s, 2H), 7.77 (s, 1H), 7.82 (s, 1H).
Sources & evidence
- ORD record
- ord-075627e4645b4c63b76ad13d000a1d3f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592460B2
Reaction notes
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