Ethyl propiolate → HCID 59252502, compound

HRID 237884Notes

Reaction equation

HRID 237884 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15]3[O:19][C:18]([NH2:20])=[N:17][CH2:16]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](OCC)(=[O:24])[C:22]#[CH:23]>C(O)C>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15]3[O:19][C:18]4=[N:20][C:21](=[O:24])[CH:22]=[CH:23][N:17]4[CH2:16]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 69039294HCID 69039294, compound

Product 1

HCID 59252502HCID 59252502, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-[2-(4-cyclohexyl-phenyl)-ethyl]-4,5-dihydro-oxazol-2-ylamine (0.134 g, 0.493 mmol) in 5 ml of ethanol was added 50 μL (0.494 mmol) of ethyl propiolate. The mixture was stirred at 80° C. for 6h and allowed to cool to room temperature. The mixture was concentrated to a solid which was purified by chromatography on silica gel eluting with ethyl acetate followed by methanol/ammonia/dichloromethane to provide 70 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated to a solid which
  2. customwas purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b3254ef57b9b47818b54dc96662b5c31
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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