4-Methylmorpholine → HCID 69203802, compound

HRID 2377239Notes

Reaction equation

HRID 2377239 reaction equation
[OH2:1].ON1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2N=N1.CN1C[CH2:17][O:16]CC1.Cl.CN(C)[CH2:22][CH2:23][CH2:24]N=C=NCC.[CH2:31]([N:33]([CH2:37][CH3:38])[CH2:34][CH2:35][NH2:36])[CH3:32]>CN(C)C=O>[CH2:31]([N:33]([CH2:37][CH3:38])[CH2:34][CH2:35][NH:36][C:17]([C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[CH2:24][CH2:23][C:22]2=[O:1])=[O:16])[CH3:32]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 60993N,N-DiethylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 69203802HCID 69203802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 26 (100 mg, 0.57 mmol) in N,N-dimethylformamide (2.8 mL) was added 1-hydroxybenzotriazole hydrate (115 mg, 0.85 mmol). The reaction mixture was cooled to 0° C. and N-methyl morpholine (187 μL, 1.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (163 mg, 0.85 mmol) were added. The reaction mixture was stirred at about 0° C. for about 15 minutes and then at about 23° C. for about 1 hour before N,N-diethylethylenediamine (88 μL, 0.62 mmol) was added. The reaction mixture was stirred overnight at about 23° C. and was then concentrated under vacuum. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (20:1) and 0.5% ammonium hydroxide as eluent to provide the desired product. MS (DCI-NH3): m/z 275 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred overnight at about 23° C.
  2. concentrationwas then concentrated under vacuum
  3. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f398ad78bafc455786fec5723e8ee6e7
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…