5-Methyl-2-(trifluoromethyl)-3-furancarboxylic acid → 6-[4-(5-METHYL-2-TRIFLUOROMETHYLFURAN-3-CARBONYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

HRID 2056498Notes

Reaction equation

HRID 2056498 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([C:11]([OH:13])=O)[CH:3]=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][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:11]([C:4]4[CH:3]=[C:2]([CH3:1])[O:6][C:5]=4[C:7]([F:8])([F:9])[F:10])=[O:13])[CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[O:21])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 27821835-Methyl-2-(trifluoromethyl)-3-furancarboxylic acidHCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 113743746-[4-(5-METHYL-2-TRIFLUOROMETHYLFURAN-3-CARBONYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

Procedure

Following the procedure of Example 9, making variations only as required to use 5-methyl-2-trifluoromethylfuran-3-carboxylic 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 solid (53% yield). m.p. 128-130° C. 1H NMR (500 MHz, CDCl3) δ 8.08, 7.99, 7.01, 6.15, 3.89-3.94), 3.77-3.82, 3.52-3.60, 2.39, 1.52, 0.71-0.80, 0.45-0.49, 0.08-0.13. MS (ES+) m/z 452 (M+1).

Sources & evidence

ORD record
ord-715d362487af4746bf33ed0375fe88b6
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

Loading…