HCID 18072498, compound → HCID 11532719, compound

HRID 552156Notes

Reaction equation

HRID 552156 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[CH:20]1([CH2:23][CH2:24][NH:25][C:26]([C:28]2[N:29]=[N:30][C:31](Cl)=[CH:32][CH:33]=2)=[O:27])[CH2:22][CH2:21]1>>[CH:20]1([CH2:23][CH2:24][NH:25][C:26]([C:28]2[N:29]=[N:30][C:31]([N:15]3[CH2:16][CH2:17][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:18])[F:19])[CH2:13][CH2:14]3)=[CH:32][CH:33]=2)=[O:27])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 18072498HCID 18072498, compoundHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 11532719HCID 11532719, compoundYield 89%

Procedure

Following the procedure as described in Example 1, making variations only as required to use piperidine-4-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 89% yield. 1H NMR (300 MHz, CDCl3) δ 8.06 (d, J=7.9 Hz, 1H), 7.96 (d, J=9.4 Hz, 2H), 7.58-7.48 (m, 3H), 7.24-7.18 (m, 1H), 6.97 (d, J=9.5 Hz, 1H), 4.53-4.49 (m, 2H), 3.54-3.47 (m, 2H), 3.18-3.00 (m, 2H), 2.66-2.57 (m, 1H), 2.07-1.99 (m, 2H), 1.93-1.79 (m, 2H), 1.49-1.43 (m, 2H), 0.73-0.67 (m, 1H), 0.45-0.39 (m, 2H), 0.07-0.02 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 172.4, 163.2, 159.9, 144.6, 134.9, 132.9, 126.9, 126.2, 126.1, 125.2, 124.9, 122.2, 112.2, 44.4, 43.8, 39.6, 34.5, 27.9, 43.8, 8.6, 4.2. MS (ES+) m/z 462 (M+1).

Sources & evidence

ORD record
ord-2fcf956970e74292a290d6bebd8d3f1a
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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