4-[2-(Trifluoromethyl)phenoxy]piperidine → N-(2-Cyclopropylethyl)-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxamide

HRID 552155Notes

Reaction equation

HRID 552155 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[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:9]3[CH2:10][CH2:11][CH:6]([O:5][C:4]4[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=4[C:2]([F:1])([F:16])[F:17])[CH2:7][CH2:8]3)=[CH:30][CH:31]=2)=[O:25])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 11590143N-(2-Cyclopropylethyl)-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxamideYield 44%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 4-(2-trifluoromethylphenoxy)piperidine 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 44% yield. 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=9.5 Hz, 1H), 7.56 (d, J=7.9 Hz, 1H), 7.46 (t, J=7.2 Hz, 1H), 7.00-6.96 (m, 3H), 4.78 (t, J=4.7 Hz, 1H), 4.03-3.95 (m, 2H), 3.83-3.74 (m, 2H), 3.56-3.50 (m, 2H), 2.00-1.98 (m, 4H), 1.51-1.45 (m, 2H), 0.75-0.70 (m, 1H), 0.46-0.40 (m, 2H), 0.09-0.04 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 163.2, 159.9, 154.9, 144.4, 133.2, 127.5, 127.4, 126.8, 120.2, 113.5, 112.1, 71.35, 41.1, 39.6, 34.6, 29.5, 8.7, 4.2 MS (ES+) m/z 457 (M+Na).

Sources & evidence

ORD record
ord-3d0a449a9f6b425fabf1a98ed19edee3
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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