1-Methylpiperazine → HCID 86626336, compound

HRID 1526060Notes

Reaction equation

HRID 1526060 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10](F)=[CH:9][C:8]=1[N:14]([C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>O1CCCC1>[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)=[CH:9][C:8]=1[N:14]([C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86626335HCID 86626335, compound

Product 1

HCID 86626336HCID 86626336, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-fluoro-2-[((S)-2-methoxy-1-methyl-ethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoic acid tert-butyl ester (2 g, 5.28 mmol) and N-methylpiperazine (5.86 mL, 52.8 mmol) in tetrahydrofuran (20 mL) was stirred at 60° C. for 7 days. The solution was then evaporated, NaHCO3 saturated solution was added and the mixture extracted with dichloromethane (3 times). The organic layer was washed with water, brine, dried over sodium sulfate filtered and evaporated to obtain a crude, which was purified by column chromatography on silica gel (dichloromethane-methanol 93:7). The title compound (2.04 g, 84%) was obtained as yellowish solid.

Workup

  1. customThe solution was then evaporated
  2. additionNaHCO3 saturated solution was added
  3. extractionthe mixture extracted with dichloromethane (3 times)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a crude, which
  9. customwas purified by column chromatography on silica gel (dichloromethane-methanol 93:7)

Sources & evidence

ORD record
ord-8a3b1f96560e4bfa9f152f54be01f8bc
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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