4-Amino-1-methylpiperidine → N2-(5-Methyl-furan-2-ylmethyl)-N5-(1-methyl-piperidin-4-yl)-quinoline-2,5-diamine

HRID 1669700Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[O:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[N:7]2.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1>O1CCOCC1>[CH3:19][C:16]1[O:15][C:14]([CH2:13][NH:12][C:6]2[CH:5]=[CH:4][C:3]3[C:2]([NH:20][CH:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (150 mg, 0.47 mmol) was dissolved in 2 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 4-Amino-1-methyl-piperidine (165 mg, 1.45 mmol), sodium tert.-butylate (117 mg, 1.22 mmol), 1,1′-bis(diphenylphosphin)ferrocen (41 mg, 0.074 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II)chloride (19 mg, 0.023 mmol) were added. The reaction mixture was stirred in a sealed tube at 120° C. overnight. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->90:10:1 gradient). The title compound was obtained as a brown solid (36 mg, 22%), MS: m/e=351.3 (M+H+).

Workup

customArgon was bubbled through the solution for 2 minutes
customto remove oxygen
customThe solvent was evaporated
customthe residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->90:10:1 gradient)

Sources & evidence

ORD record: ord-25f28c3e6fdb48b687bf47fd4ee17428
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989628B2

Reaction notes

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