Trifluoroacetic acid → Trifluoroacetic acid

HRID 474279Notes

Reaction equation

HRID 474279 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:8]=2[O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)[N:3]=1.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:8]=2[O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[N:3]=1.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66666004tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate

Product 2

HCID 6422Trifluoroacetic acidYield 293.2%HCID 666659904-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate (515 mg, 1.316 mmol) in CH2Cl2 (4 mL) was treated with TFA (2 mL, 26.0 mmol) at 0° C. The mixture was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and the residue was triturated with ether to yield a white solid, which was collected by filtration to get 4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-1-amine, TFA (440 mg, 83% yield). LC-MS (M+H)+=292.4. 1H NMR (500 MHz, methanol-d4) δ 8.99 (s, 1H), 8.11 (d, J=1.5 Hz, 1H), 8.05 (dd, J=2.1, 1.3 Hz, 2H), 4.38 (t, J=6.2 Hz, 2H), 3.07-2.94 (m, 2H), 2.48 (s, 3H), 2.02 (dd, J=8.8, 6.3 Hz, 2H), 1.84 (d, J=7.5 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was triturated with ether
  3. customto yield a white solid, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-253b04622fad482dbde70fd85dacfd63
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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