Trifluoroacetic acid → HCID 22994087, compound

HRID 1167830Notes

Reaction equation

HRID 1167830 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH:10]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:5][C:6]=1[C:7](=[S:9])[NH2:8].Br[CH2:31][C:32]([C:34]1[CH:35]=[C:36]([NH:40][C:41]([C:43]2[S:44][C:45]([Cl:48])=[CH:46][CH:47]=2)=[O:42])[CH:37]=[CH:38][CH:39]=1)=O.C(O)(C(F)(F)F)=O>CN(C=O)C.CO>[NH2:10][C:4]1[S:5][C:6]([C:7]2[S:9][CH:31]=[C:32]([C:34]3[CH:35]=[C:36]([NH:40][C:41]([C:43]4[S:44][C:45]([Cl:48])=[CH:46][CH:47]=4)=[O:42])[CH:37]=[CH:38][CH:39]=3)[N:8]=2)=[C:2]([NH2:1])[N:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 53963301HCID 53963301, compoundHCID 54012078HCID 54012078, compound

Product 1

HCID 22994087HCID 22994087, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as follows. To a solution of 1.07 g (3.0 mmol) of 4-amino-2-(trityl-amino)-thiazole-5-carbothioic acid amide (prepared analogously to the starting material described in step (ii) of Example A(1)) dissolved in DMF (12 mL), was added 5-chloro-thiophene-2-carboxylic acid (3-bromoacetyl-phenyl)-amide. After 15 minutes, the reaction was diluted with MeOH (12 mL), treated with TFA (4 mL), and stirred overnight. The resulting solution was concentrated in vacuo, diluted with ethyl acetate, extracted with 1M NaHCO3, extracted with brine, dried over MgSO4, concentrated, and purified by flash chromatography (gradient elution: 5% CH3CN/CH2Cl2 to 30% CH3CN/CH2Cl2), giving 0.47 g (36% yield) of N-[3-(2′,4′-diamino-[2,5′]bithiazolyl-4-yl)phenyl]-5-chloro-thiophene-2-carboxamide.

Workup

  1. customThe title compound was prepared
  2. concentrationThe resulting solution was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. extractionextracted with 1M NaHCO3
  5. extractionextracted with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (gradient elution: 5% CH3CN/CH2Cl2 to 30% CH3CN/CH2Cl2)

Sources & evidence

ORD record
ord-aed50fd97ca04dfdafd03158fefd8d5d
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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