octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester → octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

HRID 243625

Reaction equation

HRID 243625 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[N:17]=1)=[O:11]>CCO.CC(O)=O.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[N:17]=1)=[O:11]

Participants

5

Reactant 1

HCID 44550802octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester

Product 1

HCID 44550930octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl esterYield 72.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of compound 14 (0.391 g, 1 mmol) and Pd/C (10 wt. %, 50 mg) in EtOH and AcOH (20 ml+1 ml) was reacted under hydrogen atmosphere at 50° C. for 2 hours. The catalyst was removed by filtration through a pad of Celite. After removal of the solvent in vacuo, the crude material was dissolved in EtOAc and washed with NaHCO3 solution and brine and dried over Na2SO4. The solvent was removed by rotary evaporation. The crude solid was purified by flash chromatography (EtOAc/hexane, 2:1) to give compound 20 (0.261 g, 72.4%). 1H NMR (300 MHz, CDCl3) δ 11.2 (1H, s), 7.22 (1H, s), 7.20 (1H, s), 7.16 (1H, brs), 7.10 (1H, s), 6.70-6.66 (1H, m), 3.69 (3H, s), 2.28 (2H, t, J=7.4 Hz), 2.06 (2H, dd, J=7.3, 4.7 Hz), 1.61-1.45 (4H, m), 1.22-1.08 (4H, m). 13C NMR (75 MHz, CDCl3) δ 174.6, 171.8, 159.6, 150.1, 147.3, 135.7, 130.2, 116.9, 115.3, 113.0, 108.1, 51.9, 36.1, 34.3, 29.07, 29.01, 25.09, 25.00, 21.4.

Workup

  1. customwas reacted under hydrogen atmosphere at 50° C. for 2 hours
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe crude material was dissolved in EtOAc
  5. washwashed with NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed by rotary evaporation
  8. customThe crude solid was purified by flash chromatography (EtOAc/hexane, 2:1)

Sources & evidence

ORD record
ord-7d7cc4d73072448797ac305437d34c6e
Source dataset
uspto-grants-2014_02
Patent number
US08653278B2

Linked notes

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