Toluene → Cyclohexyl-(6-methoxy-7-morpholin-4-yl-quinoxalin-2-yl)-amine

HRID 1987496Notes

Reaction equation

C1(C)C=CC=CC=1.[CH:8]1([NH:14][C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][C:19](Br)=[C:20]([O:25][CH3:26])[CH:21]=3)[N:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CC(C)([O-])C.[Na+]>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:8]1([NH:14][C:15]2[CH:24]=[N:23][C:22]3[C:17](=[CH:18][C:19]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[C:20]([O:25][CH3:26])[CH:21]=3)[N:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

This preparation is based on an adaptation of the method described by Buchwald, et al, J. Am. Chem. Soc., 1996, 118, 7215. To a toluene solution of 2-cyclohexylamino-6-methoxy-7-bromo-quinoxaline (0.1 g, 0.3 mmol) under argon is added morpholine (0.1 g, 0.3 mmol), sodium tert-butoxide (0.04 g, 0.42 mmol), S-(−)-BINAP (cat., 0.001 g), and Pd(dba)2 (cat., 0.001 g). The reaction mixture is heated to 80° C. overnight. The mixture is cooled, diluted with Et2O, filtered, concentrated, and chromatographed (50% EtOAc/hexanes). The product is recrystallized from EtOAc/hexanes to provide, in two crops, to provide a yellow solid (m.p. 194-196° C.). Anal. Calcd. for C19H26N4O2: C, 66.64; H, 7.65; N, 16.36; Found: C, 66.60; H, 7.60; N, 16.51.

Workup

temperatureThe mixture is cooled
filtrationfiltered
concentrationconcentrated
customchromatographed (50% EtOAc/hexanes)
customThe product is recrystallized from EtOAc/hexanes
customto provide, in two crops

Sources & evidence

ORD record: ord-7a5a493867874575af0d5f7ac99f2e11
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550597B2

Reaction notes

Loading…