4-Methylmorpholine → HCID 12136647, compound

HRID 18401Notes

Reaction equation

HRID 18401 reaction equation
[C:1]12([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:19][CH:18]=1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH3:16])[C:27](=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][C:20]3[CH:19]=[CH:18][N:17]=[CH:22][CH:21]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111713164-Pyridinepentanoic acidHCID 12136646HCID 12136646, compound

Product 1

HCID 12136647HCID 12136647, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (8.4 ml) was added to a mixture of 2-(1-adamantyl)-N-propylethylamine (Intermediate No. 1-6, 0.37 g, 1.7 mmol) and 5-(4-pyridyl)valeric acid (Intermediate No. 5-1, 0.30 g, 1.7 mmol), and the whole was stirred at room temperature. N-Methylmorpholine (0.27 ml, 2.5 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.38 g, 2.0 mmol) were added thereto successively, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate (20 ml) was added to the residue, and the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (5 ml) successively. The organic layer was dried over sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography to give the target compound (0.21 g, 33%) as a colorless oily matter.

Workup

  1. stirringsuccessively, and the whole was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (20 ml)
  3. additionwas added to the residue
  4. washthe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (5 ml) successively
  5. dry with materialThe organic layer was dried over sodium sulfate, and ethyl acetate
  6. customwas evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-6d8bf1d172a74d2e9f1851c512338dc3
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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