Borane → HCID 69115084, compound

HRID 901885Notes

Reaction equation

HRID 901885 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([NH:22][C:23](=O)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:15]=2[C:31]#[N:32])[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[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:15]=2[CH2:31][NH2:32])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6331BoraneHCID 69115294HCID 69115294, compound

Product 1

HCID 69115084HCID 69115084, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 186 mg (0.39 mmol) of 4-(3-benzoylamino-2-cyano-5-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester dissolved in 10 mL tetrahydrofuran was added 1.57 mM (4 eq., 1.57 mmol) borane (1M in tetrahydrofuran). The mixture was heated to reflux overnight, cooled and quenched with methanol, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated under reduced pressure to provide 153 mg of crude 4-(2-aminomethyl-3-benzylamino-5-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. customquenched with methanol
  5. custompartitioned between ethyl acetate and water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-236eb17147b24272bceb8a3ab6f7a478
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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