Benzyl azide → ethyl 4-methyl-2-(1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)thiazole-5-carboxylate
Reaction equation
C(N=[N+]=[N-])C1C=CC=CC=1.[N:11]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[N+:12]=[N-:13].[C:25]([C:27]1[S:28][C:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:30]([CH3:32])[N:31]=1)#[CH:26]>>[CH3:32][C:30]1[N:31]=[C:27]([C:25]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=3)[CH:26]=2)[S:28][C:29]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34]Participants
4
Procedure
Following the procedure as described in Example 2, making variations as necessary to replace benzylazide with 1-(azidomethyl)-4-(trifluoromethyl)benzene to react with ethyl 2-ethynyl-4-methylthiazole-5-carboxylate, the title compound was obtained as a white solid in 67% yield: 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H), 7.66-7.55 (m, 2H), 7.45-7.39 (m, 2H), 4.29 (q, J=7.1 Hz, 2H), 5.62 (s, 2H), 2.66 (s, 3H), 1.32 (t, J=7.1 Hz, 3H); MS (ES+) m/z 397.3 (M+1).
Sources & evidence
- ORD record
- ord-d56d401b6bac45e6a0ed899324bdf9a6
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258160B2
Reaction notes
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