Trifluoroacetic acid → HCID 86708488, compound

HRID 1430802Notes

Reaction equation

HRID 1430802 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:17][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[C:2]=1[Cl:1])[C:15]#[N:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708489HCID 86708489, compound

Product 1

HCID 86708488HCID 86708488, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-chloro-5-cyano-3-(4-methylpiperazin-1-yl)phenylcarbamate (135 mg, 0.385 mmol) in DCM (1.4 mL) was added TFA (0.6 mL, 3.89 mmol). The mixture was stirred at reaction mixture. The solvent was evaporated under vacuum, the residue was dissolved in EtOAc, washed with small amount of sat NaHCO3, and brine, dried over MgSO4, filtered, concentrated, and the residue was purified by ISCO (12 g, EtOAc/DCM=0-60%) to give 82 mg of 3-amino-4-chloro-5-(4-methylpiperazin-1-yl)benzonitrile

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with small amount of sat NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by ISCO (12 g, EtOAc/DCM=0-60%)

Sources & evidence

ORD record
ord-e788185a729a4e6fa70d344624db2164
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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