Hydrochloric Acid → 2-(1-Benzothien-2-yl)-5-{[2-(1H-1,2,4-triazol-5-ylthio)butanoyl]amino}benzamide

HRID 503697Notes

Reaction equation

HRID 503697 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:25])[CH:21](Br)[CH2:22][CH3:23])=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13].[SH:26][C:27]1[N:28]=[N:29]C=[CH:31][N:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C(OCC)(=O)C.CN(C=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:25])[CH:21]([S:26][C:27]2[NH:28][N:29]=[CH:31][N:32]=2)[CH2:22][CH3:23])=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 594284882-(1-Benzothien-2-yl)-5-[(2-bromobutanoyl)amino]benzamideHCID 178527878HCID 178527878, compound

Product 1

HCID 594284892-(1-Benzothien-2-yl)-5-{[2-(1H-1,2,4-triazol-5-ylthio)butanoyl]amino}benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-Benzothien-2-yl)-5-[(2-bromobutanoyl)amino]benzamide (Example 9A; 50 mg) is introduced into DMF (1 ml) and, after addition of 3-mercapto-1,2,4-triazine (15 mg) and cesium carbonate (78 mg), stirred at RT overnight. The reaction mixture is mixed with ethyl acetate (50 ml) and 0.5N hydrochloric acid (50 ml), the aqueous phase is extracted with ethyl acetate (twice 50 ml), and the combined organic phases are washed with saturated sodium chloride solution (twice 100 ml). The organic phase is dried over magnesium sulfate and concentrated in a rotary evaporator. The residue is purified on a preparative HPLC. 14 mg (26% of theory) of the title compound are obtained.

Workup

  1. extractionthe aqueous phase is extracted with ethyl acetate (twice 50 ml)
  2. washthe combined organic phases are washed with saturated sodium chloride solution (twice 100 ml)
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator
  5. customThe residue is purified on a preparative HPLC

Sources & evidence

ORD record
ord-3623eb9cbae44fdfaa369fdba95d1308
Source dataset
uspto-grants-2010_08
Patent number
US07776922B2

Reaction notes

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