1-Oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid → 1-Oxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylic acid [4-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-3-yl]-amide
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:7]=[CH:6][C:5]=1[NH2:20])([O-:3])=[O:2].[O:21]1[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:24][C:23]([C:31](O)=[O:32])=[N:22]1>>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:17])[F:18])[N:7]=[CH:6][C:5]=1[NH:20][C:31]([C:23]1[CH2:24][C:25]2([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[O:21][N:22]=1)=[O:32])([O-:3])=[O:2]Participants
3
Procedure
The title compound was prepared from 4-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-3-ylamine (as prepared in the previous step) and 1-oxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylic acid (as prepared in Example 1, step B) according to the procedure described in Example 16, step D. 1H-NMR (400 MHz, CDCl3) δ: 9.45 (s, 1H), 8.93 (s, 1H), 7.80 (d, J=7.3 Hz, 1H), 7.65 (t, J=7.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 1H), 7.51 (d, J=7.6 Hz, 1H), 2.97 (s, 2H), 1.73-1.90 (m, 5H), 1.62-1.73 (m, 3H), 1.40-1.54 (m, 2H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H19F3N4O4: 449.1 (M+H). found: 449.2.
Sources & evidence
- ORD record
- ord-bc1f3c30088d46a4999848ee623eb1de
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232409B2
Reaction notes
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