rel-(2R,6S)-2,6-dimethylpiperazine → HCID 58988142, compound

HRID 2234975Notes

Reaction equation

HRID 2234975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:19].[CH3:20][C@H:21]1[CH2:26][NH:25][CH2:24][C@@H:23]([CH3:27])[NH:22]1>CN1CCCC1=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:25]3[CH2:24][C@H:23]([CH3:27])[NH:22][C@H:21]([CH3:20])[CH2:26]3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:19]

Participants

6

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 58988141HCID 58988141, compound

Product 1

HCID 58988142HCID 58988142, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-bromo-N-(6-bromo-2-pyridinyl)-3-fluorobenzenesulfonamide (D1) (300 mg, 0.73 mmol) and cis-2,6-dimethylpiperazine (600 mg, 5.4 mmol) in 1-methyl-2-pyrrolidinone (5 ml) and water (0.5 ml) was microwaved at 200° C. for 2000 sec. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with water (3×10 ml). The organic phase was dried and evaporated. Purification by column chromatography eluting with 5% methanol in dichloromethane afforded the title compound (D2), MS (ES+) m/e 443, 445 [M+H]+.

Workup

  1. washwashed with water (3×10 ml)
  2. customThe organic phase was dried
  3. customevaporated
  4. customPurification by column chromatography
  5. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ffaeaa4627ee44569633e11915c48e2f
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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