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

HRID 325514Notes

Reaction equation

HRID 325514 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 4 N 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 4 N 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-cd53cece0ec34d578486a213d6154ab1
Source dataset
uspto-grants-1984_04
Patent number
US04440933

Reaction notes

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