Triethylamine → HCID 19737973, compound

HRID 2255504Notes

Reaction equation

HRID 2255504 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:11]([NH2:14])(=[O:13])=[O:12])[S:5][C:6]=1[S:7]([Cl:10])(=[O:9])=[O:8].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C1COCC1>[ClH:10].[Br:1][C:2]1[CH:3]=[C:4]([S:11]([NH2:14])(=[O:13])=[O:12])[S:5][C:6]=1[S:7]([NH:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 19737946HCID 19737946, compound

Product 1

HCID 19737973HCID 19737973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from Step A (2.3 g, 6.0 mmol) in THF (5 mL) was added dropwise to a cooled solution (0° C.) of triethylamine (1.5 g) and 4-(2-aminoethyl)-morpholine (1.95 g, 15 mmol) in THF (15 mL). The solution was stirred at 0° C. for 1 h and then was warmed to ambient temperature for an additional hour. The reaction mixture was concentrated, the residue was diluted with water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (10 mL), dried and concentrated to furnish the desired product as a white solid. The material was dissolved in ethanol and treated with ethanolic HCl and the resultant solid was isolated by filtration and dried. The desired product was obtained as a white solid: mp 180°-182° C.

Workup

  1. temperaturewas warmed to ambient temperature for an additional hour
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined extracts were washed with brine (10 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9568d04a364a49d39724f9c365a98510
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

Loading…