4-Methylmorpholine → HCID 178512272, compound

HRID 865660Notes

Reaction equation

HRID 865660 reaction equation
Cl.[NH2:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1.C([O-])(O)=O.[Na+].CN1CCOCC1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=[N:41][C:42]#[N:43])OC2C=CC=CC=2)[CH:27]=1>C(O)CC.CCOC(C)=O>[C:42]([N:41]=[C:33]([NH:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH:5]=[CH:6][CH2:7]1)[NH:32][C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1)#[N:43]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 131719625158943-19-2HCID 178512277HCID 178512277, compound

Product 1

HCID 178512272HCID 178512272, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of the product from Step 4 (0.537 g, 2.74 mmol) and EtOAc was mixed with enough aqueous NaHCO3 to give a solution and the aqueous layer was extracted with EtOAc; the EtOAc extract was dried (MgSO4) and concentrated. A solution of the residue in -propanol (25 ml) was treated with N-methylmorpholine (0.75 ml, 6.86 mmol) and N-(3- pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (0.98 g, 4.12 mmol) and refluxed under N2 for 16.75 hours. The cooled reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel with 1.5% MeOH--0.15% NH4OH--CH2Cl2. The product was crystallized from EtOAc to give 3 which had m.p. 155.5°-157° C.

Workup

  1. customto give a solution
  2. extractionthe aqueous layer was extracted with EtOAc
  3. extractionthe EtOAc extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. temperaturerefluxed under N2 for 16.75 hours
  7. customThe cooled reaction mixture
  8. concentrationwas concentrated in vacuo
  9. customthe residue was chromatographed on silica gel with 1.5% MeOH--0.15% NH4OH--CH2Cl2
  10. customThe product was crystallized from EtOAc
  11. customto give 3 which

Sources & evidence

ORD record
ord-bcda0dd1e7704e998adfd59d8eff9e7b
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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