4-Methylmorpholine → HCID 10224700, compound

HRID 1063431Notes

Reaction equation

HRID 1063431 reaction equation
[C:1]1([CH:7]([N:11]2[C:16](=[S:17])[C:15]3[CH:18]=[N:19][NH:20][C:14]=3[N:13]=[CH:12]2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CN1CCOCC1.CCOC(C)=O>CN(C=O)C>[C:1]1([CH:7]([N:11]2[C:16](=[S:17])[C:15]3[CH:18]=[N:19][NH:20][C:14]=3[N:13]=[CH:12]2)[C:8]([N:30]2[CH2:31][CH2:32][N:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[CH2:28][CH2:29]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 944591-(2-Pyridyl)piperazineHCID 9814425HCID 9814425, compound

Product 1

HCID 10224700HCID 10224700, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[3-(dimethylamino)propyl]-3-ethycabodiimide HCl (1.5 eq. mmol) and following 1-hydrobenzatriazole hydrate (HOBT) (0.5 eq. mmol) was added to a solution of 2-phenyl-(4-thioxo-1,4-dihydro-pyrazolo[3,4-d]pyrimidin-5-yl) acetic acid (XIVa) (1.0 eq. mmol) and a corresponding amine such as 1-(2-pyridyl)piperazine(1.5 eq. mmol) with 4-methylmorpholine (3.0 eq. mmol) in DMF at 0° C. The resulting mixture was stirred overnight at 0° C. to room temperature. The yellow reaction mixture was filtered off and washed well with EtOAc. The filtrate was extracted with brine, saturated NaHCO3, brine. The organic layer was dried over anhydrous Na2SO4, and then was concentrated under vacuum. The crude product was chromatographed using silica gel and eluted with CH2Cl2:EtOAc/1:1 to afford (XVIi) (0.029 g, 0.07 mmol, 22% yield) as a white solid.

Workup

  1. customat 0° C
  2. filtrationThe yellow reaction mixture was filtered off
  3. washwashed well with EtOAc
  4. extractionThe filtrate was extracted with brine, saturated NaHCO3, brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationwas concentrated under vacuum
  7. customThe crude product was chromatographed
  8. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-8783029536354079814ae8203545a4f4
Source dataset
uspto-grants-2005_11
Patent number
US06964957B2

Reaction notes

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