Trifluoroacetic acid → 5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-amine

HRID 474245Notes

Reaction equation

HRID 474245 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:8]=2[O:9][CH2:10][CH2:11][CH2:12][CH:13]([NH:15]C(=O)OC(C)(C)C)[CH3:14])[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:8]=2[O:9][CH2:10][CH2:11][CH2:12][CH:13]([NH2:15])[CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70348719tert-butyl (5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)carbamate

Product 1

HCID 666655155-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-amineYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of tert-butyl (5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)carbamate (1.5 g, 3.70 mmol) in DCM (50 mL) was added TFA (5 mL). The reaction mixture was stirred at rt for 1 h. The solvent was removed under reduced pressure and treated with saturated sodium bicarbonate solution (150 mL), and extracted with ethyl acetate (2×150 mL). The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get 5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-amine (920 mg, 81%). LC-MS (M+H)+=306.2. 1H NMR: (400 MHz, CDCl3) δ ppm 8.97 (1H, s), 8.08 (1H, d, J=8.8 Hz), 8.00-7.91 (2H, m), 4.29-4.23 (2H, m), 3.27-3.25 (1H, m), 2.46 (3H, s), 2.16-2.03 (4H, m), 1.32-1.27 (3H, m).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiontreated with saturated sodium bicarbonate solution (150 mL)
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9cf13ac720fb4b3498786a1107570c08
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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