HCID 178509111, compound → HCID 178509110, compound

HRID 57274Notes

Reaction equation

HRID 57274 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=[O:22])=[CH:17][CH:16]=2)=[N:13][NH:12][C:11]=1[NH2:24]>CN(C=O)C.C(O)C.[Cl-].[NH4+].[Zn]>[NH2:24][C:11]1[NH:12][N:13]=[C:14]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][OH:22])=[CH:17][CH:16]=2)[C:10]=1[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

6

Reactant 1

HCID 178509111HCID 178509111, compound

Product 1

HCID 178509110HCID 178509110, compoundYield 4%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 4-benzothiazol-2-yl-5-(4-nitrophenyl)-2H-pyrazol-3-ylamine (218 mg, 0.65 mmol) in DMF (4 mL) and 95% ethanol (4 mL) at room temperature was added under rapid stirring a suspension of zinc powder (200 mg) in aqueous ammonium chloride (0.15 g in 2 mL of water). The resulting mixture was then stirred for 2 hrs. The residual zinc was removed by filtration and the mother liquor was poured into water (100 mL). A yellow solid was removed by filtration. The aqueous phase was extract with ethyl acetate (2×75 mL). The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting crude material was purified by preparative TLC eluting with 10:1 CH2Cl2:MeOH=10:1 to yield 7 mg (4%) of the title compound as cream coloured solid. MS (m/z, ES+): 324.1 (M+1, 100%).

Workup

  1. stirringThe resulting mixture was then stirred for 2 hrs
  2. customThe residual zinc was removed by filtration
  3. additionthe mother liquor was poured into water (100 mL)
  4. customA yellow solid was removed by filtration
  5. extractionThe aqueous phase was extract with ethyl acetate (2×75 mL)
  6. washThe combined extracts were washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting crude material was purified by preparative TLC
  11. washeluting with 10:1 CH2Cl2

Sources & evidence

ORD record
ord-630c1caf2b7148f18fb06ac60ac82edb
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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