Dimethylformamide → 2-Valeramidoisonicotinic acid morpholide

HRID 1939300Notes

Reaction equation

HRID 1939300 reaction equation
[OH:1]N1C2C=CC=CC=2N=N1.[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2CC[CH2:23][CH2:22][CH2:21]2)C[CH2:15][CH2:14][CH2:13][CH2:12]1.N1C[CH2:30][O:29][CH2:28]C1.[CH3:32][N:33]([CH3:36])[CH:34]=[O:35]>>[C:11]([NH:17][C:18]1[CH:23]=[C:22]([CH:21]=[CH:20][N:19]=1)[C:34]([N:33]1[CH2:36][CH2:30][O:29][CH2:28][CH2:32]1)=[O:35])(=[O:1])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 540118162-Valeramidoisonicotinic acid morpholide

Procedure

The compound ([9]-(94)-467') (2.4610 g) prepared in Example 98 was dissolved in anhydrous dimethylformamide (DMF) (37 ml). Then, 1-hydroxybenzotriazole (1.9477 N,N'-dicyclohexylcarbodiimide (2.9739 g), and morpholine (1.3 ml) were added to the solution. The mixture was stirred at room temperature for 16 hours. The insolubles were filtered out, and the filtrate was concentrated. The resulting residue was dissolved in chloroform, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown oil (7.4981 g). The crude oil was purified by silica gel column chromatography (Kieselgel 60=230 g, chloroform/acetone=5/1) to obtain the above-captioned compound ([9]-(94)-467") (3.1756 g) as white crystals.

Workup

  1. customThe compound ([9]-(94)-467') (2.4610 g) prepared in Example 98
  2. filtrationThe insolubles were filtered out
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe resulting residue was dissolved in chloroform
  5. washwashed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2fa88e323de84717a277367729a6c7cd
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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