2-(Chloromethyl)-4-fluoro-1-(trifluoromethyl)benzene → 6-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-CYCLOPROPYLPROPYL)AMIDE

HRID 2056539Notes

Reaction equation

HRID 2056539 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[C:6]([CH:9]=1)[CH2:7]Cl.[CH:14]1([CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:23]2[N:24]=[N:25][C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[O:22])[CH2:16][CH2:15]1>>[CH:14]1([CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:23]2[N:24]=[N:25][C:26]([N:29]3[CH2:30][CH2:31][N:32]([CH2:7][C:6]4[CH:9]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[C:10]([F:13])([F:12])[F:11])[CH2:33][CH2:34]3)=[CH:27][CH:28]=2)=[O:22])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 27591692-(Chloromethyl)-4-fluoro-1-(trifluoromethyl)benzeneHCID 668493796-Piperazin-1-yl-pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide

Product 1

HCID 670122286-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-CYCLOPROPYLPROPYL)AMIDE

Procedure

Following the procedure of Example 11, making variations only as required to use 5-fluoro-2-trifluoromethylbenzyl chloride in place of 2-trifluoromethylbenzyl chloride to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide, the title compound was obtained as a light yellow solid (34% yield). 1H NMR (300 MHz, CDCl3) δ 7.98, 7.88, 7.55-7.65, 7.2, 6.93, 3.68-3.85, 3.50, 2.60, 1.70, 1.25, 0.65, 0.40, 0.09. MS (ES+) m/z 466 (M+1).

Sources & evidence

ORD record
ord-e5bc537531e8413ca25ef2f09475fec1
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

Loading…