4,4,4-Trifluoro-3-(trifluoromethyl)crotonic acid → 6-[4-(4,4,4-TRIFLUORO-3-TRIFLUOROMETHYLBUT-2-ENOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

HRID 2356501Notes

Reaction equation

HRID 2356501 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:5](O)=[O:6].[CH:14]1([CH2:17][CH2:18][NH:19][C:20]([C:22]2[N:23]=[N:24][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[O:21])[CH2:16][CH2:15]1>>[CH:14]1([CH2:17][CH2:18][NH:19][C:20]([C:22]2[N:23]=[N:24][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:5](=[O:6])[CH:4]=[C:3]([C:8]([F:11])([F:10])[F:9])[C:2]([F:13])([F:12])[F:1])[CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[O:21])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 156694,4,4-Trifluoro-3-(trifluoromethyl)crotonic acidHCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 113172376-[4-(4,4,4-TRIFLUORO-3-TRIFLUOROMETHYLBUT-2-ENOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

Procedure

Following the procedure of Example 9, making variations only as required to use 4,4,4-trifluoro-3-trifluoromethylbut-2-enoic acid in place of 2,5-dichlorobenzoic acid to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide, the title compound was obtained as a white powder (45.4% yield). 1H NMR (CDCl3) δ 8.07, 7.97, 7.10, 7.01, 3.87-3.74, 3.58-3.50, 1.54-1.47, 0.78-0.68, 0.48-0.42, 0.10-0.05. 13C NMR (CDCl3) δ 162.8, 161.1, 159.8, 145.8, 135.2, 135.1, 127.3, 124.5, 112.7, 45.5, 44.4, 44.3, 40.9, 39.7, 34.5, 8.6, 4.2. MS (ES+) m/z 466 (M+1).

Sources & evidence

ORD record
ord-276c1804af774b37bf0385908962d237
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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