Pentylamine → HCID 11213066, compound

HRID 1661880Notes

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([NH2:12])[CH2:8][CH2:9][CH2:10][CH3:11].C[O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:40])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])[CH2:25][CH2:24]2)=[N:21][CH:22]=1)=O>O>[CH2:7]([NH:12][C:15]([C:17]1[N:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][N:26]([C:29](=[O:40])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])[CH2:27][CH2:28]2)=[N:21][CH:22]=1)=[O:14])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

Conditions

Temperature: 120 °C

Procedure

Potassium tert-butoxide (0.112 g, 1.00 mmol) was added to a premixed mixture of amylamine (2.5 mL) and 4-(2-trifluoromethylbenzoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (0.258 g, 0.65 mmol) in a 5 mL reactor for microwave oven. The reaction mixture was irradiated under stirring for 10 minutes at 120° C. On completion of the reaction, the mixture was diluted with water and extracted with dichloromethane. The organic layer was washed sequentially with 10% HCl solution, water and sodium hydroxide solution, then separated and dried with Na2SO4. Removal of the solvent afforded the title compound in 68% yield (0.200 g). 1H NMR (300 MHz, CDCl3) δ 8.85, 7.97, 7.74, 7.63, 7.56, 7.49, 7.36, 4.05-4.00, 3.89-3.82, 3.78-3.73, 3.70-3.61, 3.44-3.40, 3.33-3.31, 2.16, 1.63-1.58, 1.37-0.134.

Workup

customThe reaction mixture was irradiated
customOn completion of the reaction
extractionextracted with dichloromethane
washThe organic layer was washed sequentially with 10% HCl solution, water and sodium hydroxide solution
customseparated
dry with materialdried with Na2SO4
customRemoval of the solvent

Sources & evidence

ORD record: ord-09c3dfdda96b496bb59292521457fdb7
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030488B2

Reaction notes

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