6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide → 6-[3-(2-Trifluoromethylphenylcarbamoyl)azetidin-1-YL]-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([CH:12]1[CH2:15][NH:14][CH2:13]1)=[O:11].[CH:18]1([CH2:21][CH2:22][NH:23][C:24]([C:26]2[N:27]=[N:28][C:29](Cl)=[CH:30][CH:31]=2)=[O:25])[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][CH2:22][NH:23][C:24]([C:26]2[N:27]=[N:28][C:29]([N:14]3[CH2:15][CH:12]([C:10](=[O:11])[NH:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:16])[F:17])[CH2:13]3)=[CH:30][CH:31]=2)=[O:25])[CH2:20][CH2:19]1Participants
Procedure
Following the procedure as described in Example 1, making variations only as required to use azetidine-3-carboxylic acid (2-trifluoromethylphenyl)amide in place of piperidin-4-yl-(2-trifluoromethylphenyl)amine to react with 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide, the title compound was obtained as a white powder in 11% yield. 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=8.2 Hz, 1H), 8.02 (d, J=9.2 Hz, 1H), 8.0 (m, 1H), 7.65-7.55 (m, 3H), 7.27 (m, 1H), 6.65 (d, J=9.2 Hz, 1H), 4.4-4.5 (m, 4H), 3.75-3.65 (m, 1H), 3.6-3.5 (m, 2H), 1.5 (q, J=7.5 Hz, 2H), 0.75-0.70 (m, 1H), 0.5-0.4 (m, 2H), 0.10-0.06 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 169.9, 163.2, 160.5, 145.1, 134.5, 133.0, 126.6, 126.3, 125.2, 111.2, 55.0, 39.6, 36.0, 34.5, 8.6, 4.2. MS (ES+) m/z 434 (M+1).
Sources & evidence
- ORD record
- ord-3098a1a37b114b3992416263de3625a7
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951805B2
Reaction notes
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