HCID 23294388, compound → HCID 11676380, compound

HRID 552153Notes

Reaction equation

HRID 552153 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.N1CCC(NC2C=CC=CC=2C(F)(F)F)CC1.[CH:35]1([CH2:38][CH2:39][NH:40][C:41]([C:43]2[N:44]=[N:45][C:46](Cl)=[CH:47][CH:48]=2)=[O:42])[CH2:37][CH2:36]1>>[CH:35]1([CH2:38][CH2:39][NH:40][C:41]([C:43]2[N:44]=[N:45][C:46]([N:9]3[CH2:8][CH2:7][CH:6]([CH2:5][C:4]4[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=4[C:2]([F:1])([F:16])[F:17])[CH2:11][CH2:10]3)=[CH:47][CH:48]=2)=[O:42])[CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 23294388HCID 23294388, compoundHCID 54902682Piperidin-4-yl-(2-trifluoromethylphenyl)amineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 11676380HCID 11676380, compoundYield 35%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 4-(2-trifluoromethylbenzyl)piperidine (Vice, S. et al J. Org. Chem. 2001, 66, 2487 and references therein) 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 35% yield. 1H NMR (300 MHz, CDCl3) δ 7.98 (m, 1H), 7.96 (d, J=9.5 Hz, 1H), 7.63 (d, J=8 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 7.33-7.26 (m, 2H), 6.93 (d, J=9.5 Hz, 1H), 4.48 (d, J=13.5 Hz, 2H), 3.51 (q, J=6.5 Hz, 2H), 2.97-2.88 (m, 2H), 2.74 (d, J=6.5 Hz, 2H), 2.03-1.86 (m, 1H), 1.78 (d, J=6.5 Hz, 2H), 1.49 (q, J=6.5 Hz, 2H), 1.41-1.27 (m, 2H), 0.79-0.67 (m, 1H), 0.48-0.37 (m, 2H), 0.10-0.05 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 163.4, 160.0, 144.3, 138.6, 131.7, 131.5, 126.7, 126.4, 126.3, 126.2, 112.0, 45.3, 39.6, 39.4, 37.9, 34.6, 31.7, 8.7, 4.2. MS (ES+) m/z 433.1 (M+1).

Sources & evidence

ORD record
ord-4f0fd64da6644ef9a2af13d8416e4721
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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