Tetrahydrofuran → HCID 178428565, compound

HRID 1748569Notes

Reaction equation

HRID 1748569 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[N:6][C:7]=1[C:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH:9]=1.[F-].[K+].O1CCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[N:6][C:7]=1[C@H:8]1[CH2:13][CH2:12][C@@H:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1.[CH3:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[N:6][C:7]=1[C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 522689Potassium FluorideHCID 866924785-Methyl-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-amine

Product 2

HCID 178428565HCID 178428565, compoundHCID 178428566HCID 178428566, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

To a mixed solution of 5-methyl-6-[4-(morpholin-4-yl]cyclohex-1-en-1-yl)pyridin-3-amine (9.5 g) described in Reference Example 108, potassium fluoride (8.07 g), palladium(II) acetate (1.56 g), water (35 ml) and tetrahydrofuran (81 ml) was added poly(methylhydrosiloxane) (6.4 ml) at water temperature, and then stirred at room temperature for 2 hours. The solvent of the reaction solution was evaporated in vacuo, and the residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give the titled compounds cis-5-methyl-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (3.4 g, MS (ESI) m/z: 276 (M+H)+) and trans-5-methyl-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (2.4 g, MS (ESI) m/z: 276 (M+H)+) as white solids respectively.

Workup

  1. customThe solvent of the reaction solution was evaporated in vacuo
  2. customthe residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-694d0a7621144d6597526adb0dbddd41
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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