HCID 16244270, compound → 6-[4-(2-Trifluoromethylbenzoyl)piperidin-1-YL]-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 552152Notes

Reaction equation

HRID 552152 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[O:8])[CH2:3][CH2:2]1.[CH:19]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[N:28]=[N:29][C:30](Cl)=[CH:31][CH:32]=2)=[O:26])[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[N:28]=[N:29][C:30]([N:1]3[CH2:2][CH2:3][CH:4]([C:7](=[O:8])[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:15]([F:16])([F:17])[F:18])[CH2:5][CH2:6]3)=[CH:31][CH:32]=2)=[O:26])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 16244270HCID 16244270, compoundHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 115685106-[4-(2-Trifluoromethylbenzoyl)piperidin-1-YL]-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideYield 42%

Procedure

Following the procedure as described in Example 1, making variations only as required to use piperidin-4-yl-(2-trifluoromethylphenyl)methanone 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 42% yield. 1H NMR (300 MHz, CDCl3) δ 8.0 (d, J=10.0 Hz, 1H), 7.99 (m, 1H), 7.72 (m, 1H), 7.60 (m, 2H), 7.40 (m, 1H), 6.97 (d, J=10.0 Hz, 1H), 4.49 (m, 2H), 3.53 (q, J=7.0 Hz, 2H), 3.24-3.07 (m, 4H), 2.1-1.9 (m, 3H), 1.85-1.65 (m, 2H), 1.5 (q, J=7.0 Hz, 2H), 0.75 (m, 1H), 0.48-0.42 (m, 2H), 0.09-0.07 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 205.3, 174.6, 163.2, 159.9, 144.6, 138.9, 130.3, 128.9, 127.5, 127.1, 127.0, 121.7, 112.2, 65.8, 51.9, 48.0, 44.5, 39.6, 34.5, 27.1, 8.6, 4.2. MS (ES+) m/z 447.2 (M+1).

Sources & evidence

ORD record
ord-b0af872ee7994055b4ff55b30ba292e8
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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