Propylenediamine → (5-Fluoro-2-trifluoromethylphenyl)-{4-[5-(5-methyl-4,5-dihydro-1H-imidazol-2-YL)pyridin-2-YL]piperazin-1-YL}methanone

HRID 499181Notes

Reaction equation

HRID 499181 reaction equation
[NH2:1][CH2:2][CH:3]([NH2:5])[CH3:4].[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:30]([F:33])([F:32])[F:31])=[C:11]([CH:29]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=O)=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13]>>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:30]([F:32])([F:33])[F:31])=[C:11]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24]4[NH:5][CH:3]([CH3:4])[CH2:2][N:1]=4)=[CH:22][N:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:29]=1

Participants

3

Reactant 2

HCID 6567PropylenediamineHCID 675232816-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]nicotinic acid

Product 1

HCID 11669245(5-Fluoro-2-trifluoromethylphenyl)-{4-[5-(5-methyl-4,5-dihydro-1H-imidazol-2-YL)pyridin-2-YL]piperazin-1-YL}methanoneYield 46%

Procedure

Following the procedure as described in Example 10, making variations only as required to use 1,2-diaminopropane in place of 1,2-diaminopentane to react with 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]nicotinic acid, the title compound was obtained as a pale yellow solid in 46% yield (0.260 g). 1H NMR (300 MHz, CD3OD) δ 8.63 (d, J=2.3 Hz, 1H), 7.98-7.86 (m, 2H), 7.48-7.35 (m, 2H), 6.99 (d, J=9.2 Hz, 1H), 4.55-4.41 (m, 1H), 3.98-3.33 (m, 10H), 1.44 (d, J=6.3 Hz, 3H). MS (ES+) m/z 436 (M+1).

Sources & evidence

ORD record
ord-e83445c31e8b454ea98422b820fc57c2
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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