2-(Trifluoromethyl)benzoic acid → 6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid CYCLOBUTYLMETHYLAMIDE

HRID 2354733Notes

Reaction equation

HRID 2354733 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH:14]1([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])[CH2:17][CH2:16][CH2:15]1>>[CH:14]1([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:7])[C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[C:2]([F:1])([F:13])[F:12])[CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[O:21])[CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 98992-(Trifluoromethyl)benzoic acidHCID 668501446-Piperazin-1-yl-pyridazine-3-carboxylic acid cyclobutylmethylamide

Product 1

HCID 117192906-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid CYCLOBUTYLMETHYLAMIDE

Procedure

Following the procedure of Example 9, making variations only as required to use 2-trifluoromethylbenzoic acid in place of 2,5-dichlorobenzoic acid to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid cyclobutylmethylamide, the title compound was obtained as a white powder (45.0% yield). 1H NMR (CDCl3) δ 8.04, 7.83, 7.72, 7.64-7.51, 7.32, 7.00, 4.10-4.01, 3.90-3.66, 3.49-3.27, 2.63-2.47, 2.11-1.67. 13C NMR (CDCl3) δ 167.7, 162.9, 159.8, 145.4, 134.2, 132.4, 129.6, 127.4, 126.9, 126.8, 125.4, 121.8, 112.8, 46.4, 44.6, 41.2, 35.1, 25.7, 18.3. MS (ES+) m/z 448 (M+1).

Sources & evidence

ORD record
ord-cee6ee4b142648618b888cf0efa9bd2e
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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