Trifluoroacetic acid → 2-(4-nitro-1H-pyrazol-1-yl)ethanamine-TFA salt

HRID 624026Notes

Reaction equation

HRID 624026 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[N:11]1)(C)(C)C.[C:19]([OH:25])([C:21]([F:24])([F:23])[F:22])=[O:20]>C(Cl)Cl>[OH:25][C:19]([C:21]([F:24])([F:23])[F:22])=[O:20].[N+:15]([C:13]1[CH:12]=[N:11][N:10]([CH2:9][CH2:8][NH2:7])[CH:14]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70984700tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

Product 1

HCID 867042092-(4-nitro-1H-pyrazol-1-yl)ethanamine-TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of tert-butyl(2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate (5.50 g, 21.49 mmol) in DCM (55 mL), TFA (20 mL, 261.16 mmol) was added dropwise. The resulting solution was stirred at 0° C. for 3 h, then the reaction mixture was concentrated in vacuo to obtain 2-(4-nitro-1H-pyrazol-1-yl)ethanamine-TFA salt as an off-white paste, which was used in the next step without further purification. LC-MS conditions A: tR=0.21 min, no ionization.

Workup

  1. additionwas added dropwise
  2. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-101cdd90e972465c9332bf01f817215c
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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