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

HRID 499180Notes

Reaction equation

HRID 499180 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]([F:28])([F:27])[F:26])=[C:6]([CH:24]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=O)=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[O:8].[NH2:29][CH2:30][CH:31]([NH2:35])[CH2:32][CH2:33][CH3:34]>O=P(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]([F:28])([F:27])[F:26])=[C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]4[NH:35][CH:31]([CH2:32][CH2:33][CH3:34])[CH2:30][N:29]=4)=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[O:8])[CH:24]=1

Participants

4

Reactant 2

HCID 14637946Pentane-1,2-diamineHCID 675232816-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]nicotinic acid

Product 1

HCID 67523309(5-Fluoro-2-trifluoromethylphenyl)-{4-[5-(5-propyl-4,5-dihydro-1H-imidazol-2-YL)pyridin-2-YL]piperazin-1-YL}methanoneYield 9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To a stirred solution of 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]nicotinic acid (0.509 g, 1.281 mmol) in POCl3(10 mL) was added dropwise 1,2-diaminopentane (3.50 g, 34.0 mmol). The resulting mixture was stirred at reflux for 16 h and then allowed to cool to ambient temperature and concentrated. The residue was taken up in saturated NaHCO3 and extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by chromatography to afford the title compound in 9% yield (0.052 g). 1H NMR (300 MHz, CDCl3) δ 9.09 (d, J=2.2 Hz, 1H), 8.56 (dd, J=2.2, 9.2 Hz, 1H), 7.74 (dd, J=5.1, 8.8 Hz, 1H), 7.22 (d, J=7.8 Hz, 1H), 7.10 (dd, J=2.4, 8.0 Hz, 1H), 6.65 (d, J=9.2 Hz, 1H), 4.32-3.49 (m, 9H), 1.92-0.75 (m, 9H). MS (ES+) m/z 464 (M+1).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-129125d8fca948129eabd82be1123389
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

Loading…