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

HRID 2117899Notes

Reaction equation

HRID 2117899 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)=[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].C(O)(C(F)(F)F)=O>>[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=2)=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21915095HCID 21915095, compound

Product 1

HCID 219146932-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-(4-nitrobenzyl)-1,3-thiazole-5-carboxamideYield 84.1%

Procedure

tert-Butyl {4-[2-(2-(acetylamino)-5-{[(4-nitrobenzyl)amino]carbonyl}-1,3-thiazol-4-yl)ethyl]phenyl}carbamate (135 mg) and TFA (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 MeOH and CHCl3, and made basic (pH=8) by 1N—NaOH. The mixture was concentrated in vacuo. The residual solid was washed with water to give 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-(4-nitrobenzyl)-1,3-thiazole-5-carboxamide (92.5 mg) as a pale yellow solid.

Workup

  1. customwere combined at 0° C
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH
  4. concentrationThe mixture was concentrated in vacuo
  5. washThe residual solid was washed with water

Sources & evidence

ORD record
ord-1515946e5fb547448e92eac64e39b74c
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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