Reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([S:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][N:24]=3)[C:20]#[N:21])[CH:13]=[CH:14][CH:15]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].Cl.C(N(CC)CC)C>>[OH:30][C:5]1[C:6]([CH2:27][CH2:28][CH3:29])=[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16][C:17]3[CH:18]=[C:19]([C:20]4[N:31]=[N:32][NH:33][N:21]=4)[CH:22]=[CH:23][N:24]=3)[CH:11]=2)[CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2]Participants
4
Procedure
Employing the procedure essentially as described in Example 1 using 2-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-isonicotinonitrile (380 mg, 0.908 mmol), sodium azide (590 mg, 9.08 mmol), and triethylamine hydrochloride (1.25 g, 9.08 mmol), the title compound is obtained as a white solid (261 mg, 62%): 1H NMR (DMSO-d6) δ 0.760 (t, 3H), 1.39 (sextuplet, 2H), 2.52 (t, 2H), 2.56 (s, 3H), 5.32 (s, 2H), 6.71 (d, 1H), 7.59 (m, 4H), 7.73 (m, 2H), 7.79 (d, 1H), 8.64 (d, 1H), 12.82 (s, 1H); MS (esi negative) m/z 460 (m−1).
Sources & evidence
- ORD record
- ord-30d6854ae7964fc5bdc621314bf9741d
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858646B2
Linked notes
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