1,3,4-Thiadiazole, 2-amino-5-methyl- → HCID 15158115, compound

HRID 703974Notes

Reaction equation

HRID 703974 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=O.[NH2:20][C:21]1[S:22][C:23]([CH3:26])=[N:24][N:25]=1>C(O)CCC>[CH3:26][C:23]1[S:22][C:21]2=[N:20][C:3]([C:5]3[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:7][N:8]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=34)=[CH:2][N:25]2[N:24]=1

Participants

4

Reactant 2

HCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 15158181HCID 15158181, compound

Product 1

HCID 15158115HCID 15158115, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-(2-bromoacetyl)-2-phenylpyrazolo[1,5-a]pyridine (1.87 g), 2-amino-5-methyl-1,3,4-thiadiazole (0.68 g) and 1-butanol (19 ml) was refluxed for 5 hours and 20 minutes. The reaction mixture was evaporated in vacuo and the residue was taken up methylene chloride (40 ml). The methylene chloride solution was washed with an aqueous solution of potassium carbonate and dried over magnesium sulfate. The solvent was removed and the residue was subjected to chromatography on silica gel (25 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 3-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (1.06 g), which was recrystallized from acetone gave crystals (0.69 g).

Workup

  1. temperaturewas refluxed for 5 hours and 20 minutes
  2. customThe reaction mixture was evaporated in vacuo
  3. washThe methylene chloride solution was washed with an aqueous solution of potassium carbonate
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. additionThe fractions containing the objective compound
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-43ead621f30840d0957a1729b7b2743e
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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