Trifluoroacetic acid → 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-methyl-1,3-thiazole-5-carboxamide

HRID 1246486Notes

Reaction equation

HRID 1246486 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OC(C)(C)C)=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>>[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21915076HCID 21915076, compound

Product 1

HCID 219151182-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-methyl-1,3-thiazole-5-carboxamideYield 67.8%

Procedure

tert-Butyl 4-(2-{2-(acetylamino)-5-[(methylamino)carbonyl]-1,3-thiazol-4-yl}ethyl)phenylcarbamate (95 mg) and trifluoroacetic acid (2 ml) were combined at 0° C. The reaction mixture was stirred at room temperature for an hour, and concentrated in vacuo. The residue was dissolved in chloroform. The organic solution was washed with 1N sodium hydroxide solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative silica gel column chromatography with chloroform/methanol (10:1) as an eluent to give 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-methyl-1,3-thiazole-5-carboxamide (49 mg) as an off-white amorphous substance.

Workup

  1. customwere combined at 0° C
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. washThe organic solution was washed with 1N sodium hydroxide solution, water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative silica gel column chromatography with chloroform/methanol (10:1) as an eluent

Sources & evidence

ORD record
ord-724c85e4f2a54832a731b64d3f119c1c
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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