Triethylamine → 3-Amino-4-[3-(6-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole

HRID 1982230Notes

Reaction equation

HRID 1982230 reaction equation
Cl.Cl.Cl.[N:4]1([CH2:10][C:11]2[N:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:26])[C:23](=[NH:25])[NH2:24])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[S:34](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O>C(Cl)Cl>[NH2:25][C:23]1[C:22]([NH:21][CH2:20][CH2:19][CH2:18][O:17][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:10][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[N:16]=2)=[N:26][S:34][N:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478601HCID 178478601, compound

Product 1

HCID 133136983-Amino-4-[3-(6-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the crude product prepared in Step B in 80 ml of CH2Cl2 and containing 7.69 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (7.35 g; 18.5 mmoles). After stirring at ambient temperature for one hour, the mixture was washed with 50 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 100 g of silica gel (230-400 mesh) using ethyl acetate-methanol (95:5) as the eluent to give 3.63 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 salt of the title compound, mp 125.5°-131° C.

Workup

  1. washthe mixture was washed with 50 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 100 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-574cdfa901ba421eb29544e6cc4b401d
Source dataset
uspto-grants-1986_06
Patent number
US04595758

Reaction notes

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