Cesium carbonate → 5-Methyl-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-amine

HRID 1748529Notes

Reaction equation

C(CC(=O)C)(=O)C.O.[NH3:9].Br[C:11]1[CH:12]=[C:13]([CH3:29])[C:14]([C:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH2:19][CH:18]=2)=[N:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O.[Cu]>[CH3:29][C:13]1[CH:12]=[C:11]([NH2:9])[CH:16]=[N:15][C:14]=1[C:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Acetylacetone (0.31 ml) and 28% ammonia water (1.78 ml) were added to a suspension of 4-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]morpholine (2 g), copper acetylacetonate (466 mg) and cesium carbonate (3.86 g) in N,N-dimethylformamide (12 ml), sealed in a tube under nitrogen atmosphere and stirred at 100° C. for 20 hours. After completion of the reaction, the reaction solution was left stand to room temperature and concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chlorofolin/methanol) to give the titled compound (1.31 g) as a pale yellow solid.

Workup

customsealed in a tube under nitrogen atmosphere
customAfter completion of the reaction
waitthe reaction solution was left stand to room temperature
concentrationconcentrated
additionThe resulting residue was diluted with water
extractionextracted with chloroform
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated
customThe resulting residue was purified with silica gel column chromatography (chlorofolin/methanol)

Sources & evidence

ORD record: ord-849469cc25c44838980b3b80b07f071e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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