1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 10255391, compound

HRID 2371423Notes

Reaction equation

HRID 2371423 reaction equation
[O:1]=[C:2]1[CH:7]([CH2:8][C:9]([OH:11])=O)[S:6](=[O:13])(=[O:12])[C:5]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:4]=2[NH:3]1.O.OC1C2N=NNC=2C=CC=1.[CH3:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][O:42][CH3:43].Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O>[CH3:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][N:39]([CH2:40][CH2:41][O:42][CH3:43])[C:9](=[O:11])[CH2:8][CH:7]1[S:6](=[O:13])(=[O:12])[C:5]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:4]=2[NH:3][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10359893HCID 10359893, compoundHCID 147267702-Methoxy-N-[2-(2-methoxyethoxy)ethyl]ethan-1-amineHCID 178526939HCID 178526939, compound

Product 1

HCID 10255391HCID 10255391, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazin-3-yl)acetic acid (3 g, 9 mmol) in dry DMF (25 ml) was added hydroxybenzotriazole hydrate (1.22 g, 9 mmol), N-methoxyethoxyethyl-N-methoxyethylamine (3.19 g, 18 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.59 g, 14 mmol), and the resulting reaction mixture was stirred overnight. Water (10 ml) was added, the mixture stirred an additional 2 hours and concentrated to dryness under reduced pressure. The residue was treated with 0.5N HCl and the pH adjusted to 6.5-6.9 by the additon of dilute NH4OH. The aqueous mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried over sodium sulfate. After filtration and removal of the solvent, the residue was recrystallized from water to give N-methoxyethoxyethyl-N-methoxyethyl-(2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetamide, mp 156°-158° C.

Workup

  1. customthe resulting reaction mixture
  2. stirringthe mixture stirred an additional 2 hours
  3. concentrationconcentrated to dryness under reduced pressure
  4. additionThe residue was treated with 0.5N HCl
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. washthe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration and removal of the solvent
  9. customthe residue was recrystallized from water

Sources & evidence

ORD record
ord-04f7e38958c84bc0a7867d1049f69627
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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