2-Methoxyethanol → HCID 87549821, compound

HRID 1895973Notes

Reaction equation

HRID 1895973 reaction equation
[CH3:1][O:2][CH2:3]CO.[C:6]([O:13]C(Cl)(Cl)Cl)([O:8][C:9](Cl)(Cl)Cl)=O.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][CH:27]=[C:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[N:20]=1>C(Cl)Cl>[CH3:18][C:19]1[N:20]=[C:21]([C:25]#[C:26][CH:27]=[C:28]2[CH2:29][CH2:30][N:31]([C:6]([O:8][CH2:9][CH2:3][O:2][CH3:1])=[O:13])[CH2:32][CH2:33]2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 94429TriphosgeneHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87549821HCID 87549821, compoundYield 145%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-methoxyethanol (26.9 μl, 0.34 mmol) and ditrichloromethyl carbonate (37.2 mg, 0.125 mmol) in CH2Cl2 (1.5 mL) stirred at r.t., was added dropwise a solution of DEA (139 μL, 0.814 mmol) in 1.5 mL of CH2Cl2 over 30′. After 40 min., was added a solution of the Compound of Example 3 (72 mg, 0.339 mmol) and 70 μL of DEA in 0.8 mL of CH2Cl2. After 24 h, the reaction mixture was evaporated to dryness in vacuo and the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc gradient from 7:3 to 3:7 to afford the title compound (57 mg).

Workup

  1. waitAfter 24 h
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. customthe residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  4. washeluting with Petroleum Ether-EtOAc gradient from 7:3 to 3:7

Sources & evidence

ORD record
ord-6c8ac7ad5ed74fd1b4eae89a40533c0d
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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