HCID 58905645, compound → HCID 58905640, compound

HRID 1294076Notes

Reaction equation

HRID 1294076 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])[S:10][C:6]=2[CH:5]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[CH:3]=1>CC(O)=O.[Zn]>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])[S:10][C:6]=2[CH:5]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 58905645HCID 58905645, compound2×

Product 1

HCID 58905640HCID 58905640, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl (4-bromo-6-(4-nitrophenoxy)benzthiazole-2-yl)carbamate (Intermediate 10F-65.3 mg, 0.15 mmol) in AcOH (2 mL) was added Zn powder (300 mg) and stirred at room temperature for 2 hrs. The insoluble materials were removed by filtration. The solvent was removed by evaporation. The residue was charged on SCX column chromatography then washed with MeOH then eluted with NH3—MeOH to give the title compound (39.6 mg, 65%): MS m/e 394, 396 (M+1).

Workup

  1. customThe insoluble materials were removed by filtration
  2. customThe solvent was removed by evaporation
  3. additionThe residue was charged on SCX column chromatography
  4. washthen washed with MeOH
  5. washthen eluted with NH3—MeOH

Sources & evidence

ORD record
ord-a28293ed90b34685a6da4f81719d9361
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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