4-Methylmorpholine → HCID 68955800, compound

HRID 1455280Notes

Reaction equation

HRID 1455280 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[C:9]([CH2:19][CH3:20])=[N:10][N:11]([CH2:15][C:16]([OH:18])=O)[C:12]=2[CH2:13][CH3:14])=[CH:5][CH:4]=1)#[N:2].[C:23]([NH:26][NH2:27])(=[O:25])[CH3:24].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[C:23]([NH:26][NH:27][C:16](=[O:18])[CH2:15][N:11]1[C:12]([CH2:13][CH3:14])=[C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][CH:21]=2)[C:9]([CH2:19][CH3:20])=[N:10]1)(=[O:25])[CH3:24]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14039AcetohydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68919233HCID 68919233, compound

Product 1

HCID 68955800HCID 68955800, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The acid of step (a) above (400 mg, 1.34 mmol), acetic hydrazide (109 mg, 1.47 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (372 mg, 1.47 mmol), 1-hydroxybenzotriazole hydrate (192 mg, 1.47 mmol) and N-methylmorpholine (525 mg, 5.36 mmol) were stirred in N,N-dimethylformamide (6 ml) at room temperature for 18 hours. The reaction mixture was then evaporated under reduced pressure and the residue was partitioned between dichloromethane (40 ml) and water (30 ml). The organic layer was dried over magnesium sulphate, filtered, and then concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (93:7:0.5, by volume) to provide the title compound (345 mg, 72%).

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (40 ml) and water (30 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (93:7:0.5, by volume)

Sources & evidence

ORD record
ord-bff69c5578064a97aae3116016fe7011
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

Loading…