Acetic Acid → HCID 21915174, compound

HRID 1246436Notes

Reaction equation

HRID 1246436 reaction equation
[CH3:1][CH:2]([CH3:22])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[N:10]=1)=[O:4].C(O)(=O)C.CO>[Pd].O1CCCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][C:9]2[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH3:22])[S:7][CH:8]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 219151012-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide

Product 1

HCID 21915174HCID 21915174, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide (333 mg), palladium on carbon (33 mg), acetic acid (1 ml), methanol (2 ml) and tetrahydrofuran (2 ml) was stirred under hydrogen atmosphere (4 atm) at ambient temperature for 5 hours. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 5% methanol/ethyl acetate as an eluent. The solid residue was collected and washed with diisopropyl ether to give N-{4-[2-(4-aminophenyl)ethyl]-1,3-thiazol-2-yl}-2-methylpropanamide (260 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel with 5% methanol/ethyl acetate as an eluent
  4. customThe solid residue was collected
  5. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-0f14644031754b9583720edd58ddf1ad
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

Loading…