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

HRID 2371423노트

반응식

HRID 2371423 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 10255391HCID 10255391, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-04f7e38958c84bc0a7867d1049f69627
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093332

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