Triethylamine → 7-[(2,3-Dichlorophenyl)carbonyl]-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889109Notes

Reaction equation

HRID 1889109 reaction equation
[S:1]1[C:5]([C:6]2[N:10]3[CH2:11][CH2:12][NH:13][CH2:14][C:9]3=[N:8][N:7]=2)=[N:4][CH:3]=[N:2]1.C(N(CC)CC)C.[Cl:22][C:23]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C([O-])(O)=O.[Na+]>ClCCl.CO.C(OCC)(=O)C>[Cl:22][C:23]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([N:13]1[CH2:12][CH2:11][N:10]2[C:6]([C:5]3[S:1][N:2]=[CH:3][N:4]=3)=[N:7][N:8]=[C:9]2[CH2:14]1)=[O:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 179442,3-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 665987953-(1,2,4-Thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 665991627-[(2,3-Dichlorophenyl)carbonyl]-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (I115) (50 mg, 0.240 mmol) and triethylamine (0.050 mL, 0.360 mmol) in Dichloromethane (DCM) (1.5 mL) was treated with 2,3-dichlorobenzoyl chloride (55.3 mg, 0.264 mmol, commercially available) and stirred at room temp for 1 hr. After 1 hr, 2 drops of methanol and then NaHCO3 solution (5 ml) and ethyl acetate (30 ml) were added and the product was extracted into the ethyl acetate which was dried (Na2SO4) and concentrated. Purification by high pH MDAP gave desired material as a white solid in 76 mg.

Workup

  1. waitAfter 1 hr
  2. extractionthe product was extracted into the ethyl acetate which
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by high pH
  6. customMDAP gave desired material as a white solid in 76 mg

Sources & evidence

ORD record
ord-457da5fa8c7340e4825c45baa5e08e57
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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