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

HRID 483260Notes

Reaction equation

HRID 483260 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-24536a55c7c44d1c947478dd3b498c8b
Source dataset
uspto-grants-1986_03
Patent number
US04578471

Reaction notes

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