Dimethyl Sulfide → HCID 69115564, compound

HRID 901860Notes

Reaction equation

HRID 901860 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=O)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:15]=2[C:30]#[N:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:15]=2[CH2:30][NH2:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 1068Dimethyl SulfideHCID 69114968HCID 69114968, compound

Product 1

HCID 69115564HCID 69115564, compoundYield 68.5%

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[2-cyano-3-(2-fluorobenzoylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (1.282 g, 3.02 mmol) was added BH3.DMS (10M in THF). Aftering heating at 70° C. in an open flask for 20 minutes to remove the dimethyl sulfide, the reaction was then heated under reflux for 4 hours. To the cooled solution was added MeOH slowly and the resulting mixture was stirred at room temperature for an hour. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 4-[2-aminomethyl-3-(2-fluoro-benzylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (858 mg, 67%). MS (M+H)+:415.3

Workup

  1. customto remove the dimethyl sulfide
  2. temperaturethe reaction was then heated
  3. temperatureunder reflux for 4 hours
  4. additionTo the cooled solution was added MeOH slowly
  5. customThe reaction mixture was partitioned between water and ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialAfter drying over MgSO4
  8. concentrationthe organic fraction was concentrated in vacuo
  9. customresulting brown residue
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-832ee40d5638460282a8742134d5cbb6
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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