HCID 12069418, compound → HCID 12069416, compound

HRID 413784Notes

Reaction equation

HRID 413784 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([C:9]1[CH:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][C:10]=1[N+:17]([O-])=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:20])[N:7]([C:9]1[CH:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH2:17])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 12069418HCID 12069418, compound

Product 1

HCID 12069416HCID 12069416, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst3×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-nitro-5-methylthiophenyl)-N-methylcarbamic acid t-butyl ester (obtained in Reference Example 3) in anhydrous methanol (120 ml) and anhydrous tetrahydrofuran (30 ml) was added 10% palladium on carbon (3.0 g). The resulting mixture was vigorously stirred under a hydrogen atmosphere. Further 10% palladium on carbon (1.5 g) was added after 2.5 hours and 4.5 hours of the reaction respectively. The resulting mixture was stirred at room temperature for 1.5 hours and allowed to stand overnight. 10% palladium on carbon (0.7 g) was further added to the reaction mixture, which was then stirred under a hydrogen atmosphere for 1 hour. At the end of this time the 10% palladium on carbon was filtered off and the filtrate concentrated in vacuo. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (⅓) as the eluant to afford the desired compound (3.61 g). Rf=0.24 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (⅓) as the eluant).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1.5 hours
  2. stirringwas then stirred under a hydrogen atmosphere for 1 hour
  3. filtrationAt the end of this time the 10% palladium on carbon was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-44f11938685f400cb5ca943f53dfc568
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

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