HCID 23023993, compound → HCID 23023940, compound

HRID 1373851Notes

Reaction equation

HRID 1373851 reaction equation
[CH3:1][N:2]([CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[N:7]=1>C(O)C.O1CCCC1.[C].[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:7]=[C:3]([N:2]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=3)[CH3:1])[S:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 23023993HCID 23023993, compound

Product 1

HCID 23023940HCID 23023940, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 4-(N-methyl-N-(4-(4-nitrophenyl)-2-thiazolyl)aminomethyl)benzoate (200.0 g, 0.522 mol) obtained in Example 1(3) in a mixture of ethanol (800 ml, 4.0 v/w) and tetrahydrofuran (800 ml, 4.0 v/w) was added 10% palladium carbon (20.0 g) and the mixture was stirred overnight under a hydrogen atmosphere at 3 atm. The reaction mixture was filtered through celite and 10% palladium carbon (20.0 g) was added to the filtrate. The mixture was stirred under a hydrogen atmosphere at 3 atm for 3 hr. After celite filtration and solvent evaporation, toluene (800 ml) was added to the residue and the solvent was evaporated to give the title compound (182.5 g, yield 99.0%) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite and 10% palladium carbon (20.0 g)
  2. additionwas added to the filtrate
  3. stirringThe mixture was stirred under a hydrogen atmosphere at 3 atm for 3 hr
  4. filtrationAfter celite filtration and solvent evaporation, toluene (800 ml)
  5. additionwas added to the residue
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1415eb6a097847278ff7ec504d7413a3
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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