Borane → 4-(2-Aminomethyl-3-benzylamino-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 901878Notes

Reaction equation

HRID 901878 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]=2[C:29]#[N:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]=2[CH2:29][NH2:30])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6331BoraneHCID 588241264-(3-Benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 588241244-(2-Aminomethyl-3-benzylamino-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 288 mg (0.7 mmol) of 4-(3-benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester dissolved in 7 mL tetrahydrofuran was added 1.4 mL (2 eq., 1.4 mmol, 1M in tetrahydrofuran) borane. The mixture was refluxed 10 hours and quenched with methanol, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated to yield crude 4-(2-aminomethyl-3-benzylamino-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester, which was used directly in the following step.

Workup

  1. temperatureThe mixture was refluxed 10 hours
  2. customquenched with methanol
  3. custompartitioned between ethyl acetate and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59043d04d93f4285a3c21271d8c1aae1
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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