Potassium Carbonate → HCID 178463213, compound

HRID 1527797Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:22][CH3:23])[C@H:14]2[CH2:19][CH2:18][C@H:17]([NH:20][CH3:21])[CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:25][CH2:26][O:27][CH3:28].C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:22][CH3:23])[C@H:14]2[CH2:19][CH2:18][C@H:17]([N:20]([CH2:25][CH2:26][O:27][CH3:28])[CH3:21])[CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of crude methyl 5-bromo-3-(ethyl((trans)-4-(methylamino)cyclohexyl)amino)-2-methylbenzoate (25 g, 65.44 mmol), 1-bromo-2-methoxyethane (18.19 g, 130.8 mmol) in acetonitrile (250 mL), K2CO3 (18.06 g, 130.8 mmol) and KI (6.51 g, 39.21 mmol) were added. The resulting reaction mass was stirred at 65° C. for 16 h. On completion, reaction mixture was diluted with water (300 mL) and extracted with DCM (500 mL×3). The combined organic layers were washed with water, dried over Na2SO4 and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography to afford the title compound (20 g, 69.3% yield).

Workup

customThe resulting reaction mass
customOn completion, reaction mixture
extractionextracted with DCM (500 mL×3)
washThe combined organic layers were washed with water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude compound was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-507e58eedf0c44fa9321d31ce97331cf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09089575B2

Reaction notes

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