Morpholine → HCID 59506284, compound

HRID 1098763Notes

Reaction equation

HRID 1098763 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([Br:13])[CH:5]=1)(=[O:3])[CH3:2].[B-](F)(F)(F)F.[CH3:19][CH2:20][O:21][C:22]([C:24](C#N)=[N:25]OC(N(C)C)=[N+](C)C)=O.N1CCOCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:13][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:12]=[CH:11][C:7]=1[C:8]([N:25]1[CH2:19][CH2:20][O:21][CH2:22][CH2:24]1)=[O:10]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13347277HCID 13347277, compound

Product 1

HCID 59506284HCID 59506284, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product obtained in step 3 (230 mg, 0.95 mmol) and TOTU (310 mg, 0.95 mmol) in DMF (2 mL) was added morpholine (83 μL, 0.95 mmol) and DIPEA (162 μL, 0.95 mmol). The reaction mixture was stirred for 2 h at RT. Ethyl acetate (20 ml) and water (20 ml) was added, the organic phase was separated and washed with hydrochloric acid (1 M, 20 ml), water (20 ml), brine (2×20 ml) and dried over Na2SO4. After evaporation and flash-chromatography the product was obtained as oil (160 mg, 54%).

Workup

  1. customthe organic phase was separated
  2. washwashed with hydrochloric acid (1 M, 20 ml), water (20 ml), brine (2×20 ml)
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation and flash-chromatography the product

Sources & evidence

ORD record
ord-4c95c90a1d6e4051abd9ed8da27e600a
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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