4-Methylmorpholine → HCID 9857142, compound

HRID 1977433Notes

Reaction equation

HRID 1977433 reaction equation
[OH2:1].ON1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2N=N1.[NH4+:12].[Cl-:13].[CH3:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.Cl.CN(C)CCCN=C=N[CH2:30][CH3:31].[C:33]([O-:36])(O)=O.[Na+]>CN(C=O)C>[Cl:13][C:6]1[CH:11]=[CH:10][C:9]([O:36][C:33]2[CH:14]=[N:15][CH:20]=[C:19]3[O:18][C:17]([C:16]([NH2:12])=[O:1])=[CH:30][C:31]=23)=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 9857142HCID 9857142, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 327B (0.15 g, 0.5 mmol) in DMF (10 mL) was treated with 1-hydroxybenzotriazole hydrate (0.104 g, 0.66 mmol), NH4Cl (0.0948 g, 0.017 mmol), and 4-methylmorpholine (0.141 g, 0.14 mmol). The solution was cooled to 0° C. and treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.115 g, 0.6 mmol), warmed to room temperature, stirred overnight, poured into saturated NaHCO3, filtered, washed with brine (3×20 mL), dried (MgSO4), and evaporated. Purification by flask chromatography on silica gel eluting with 20% acetone-hexane yielded 0.030 g (21%) of the title compound as a glassy residue.

Workup

  1. temperaturewarmed to room temperature
  2. filtrationfiltered
  3. washwashed with brine (3×20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by flask chromatography on silica gel eluting with 20% acetone-hexane

Sources & evidence

ORD record
ord-f19f9045d51342d88ed7b8188682e740
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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