Trifluoroacetic acid → Trifluoroacetic acid

HRID 921859Notes

Reaction equation

HRID 921859 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:6][C:5]([C:18]#[N:19])=[CH:4][C:3]=1[NH:20]C(=O)OC(C)(C)C.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[NH2:20][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:2]=1[Cl:1])[C:18]#[N:19].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734943Tert-butyl (2-chloro-5-cyano-3-(3-(4-methylpiperazin-1-yl)propyl)phenyl)carbamate

Product 2

HCID 6422Trifluoroacetic acidYield 617.4%HCID 899230483-Amino-4-chloro-5-(3-(4-methylpiperazin-1-yl)propyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (2-chloro-5-cyano-3-(3-(4-methylpiperazin-1-yl)propyl)phenyl)carbamate (49 mg, 0.125 mmol) was taken up in DCM (0.8 mL) and TFA (0.192 mL, 2.494 mmol) was added. The reaction was stirred at room temperature for 1 h. The solvent was removed in vacuo and the material azeotroped 2× with toluene. The material was dried under vacuum overnight. 3-amino-4-chloro-5-(3-(4-methylpiperazin-1-yl)propyl)benzonitrile, TFA (88 mg) was obtained as an off-white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe material azeotroped 2× with toluene
  3. customThe material was dried under vacuum overnight

Sources & evidence

ORD record
ord-b4623de32d8a4eea8a9a3c48272356df
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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