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2,2'-Thiobis(1H-isoindole-1,3(2H)-dione) → 3-Amino-4-[3-(4-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole

HRID 483260
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 483260
Cl.Cl.Cl.[N:4]1([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:26])[C:23](=[NH:25])[NH2:24])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[S:27](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O>C(Cl)Cl.C(N(CC)CC)C>[NH2:25][C:23]1[C:22]([NH:21][CH2:20][CH2:19][CH2:18][O:17][C:13]2[CH:12]=[C:11]([CH2:10][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:16]=[CH:15][N:14]=2)=[N:26][S:27][N:24]=1
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Komponenten

5

Edukt 2

HCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478602HCID 178478602, Verbindung

Produkt 1

HCID 133136993-Amino-4-[3-(4-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of the product prepared in Step C in 50 ml of CH2Cl2 and 5.7 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (5.44 g; 13.7 mmoles). After stirring at ambient temperature for one hour, the mixture was washed with 40 ml of 4N NaOH, water, saturated aqueous NaCl solution, dried (Na2SO4), filtered and evaporated under reduced pressure to give the crude product. The product was purified by flash chromatography on 90 g of silica gel (230-400 mesh) using ethyl acetate-methanol (96:4) as the eluent to give 3.44 g of the title compound as a viscous oil. Treatment of the product with one equivalent of cyclohexyl sulfamic acid in acetone gave the cyclohexyl sulfamate of the title compound, mp 124.5°-126° C.

Aufarbeitung

  1. washthe mixture was washed with 40 ml of 4N NaOH, water, saturated aqueous NaCl solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give the crude product
  6. customThe product was purified by flash chromatography on 90 g of silica gel (230-400 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-24536a55c7c44d1c947478dd3b498c8b
Quelldatensatz
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04578471

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