Water → HCID 67231452, compound

HRID 2047495Notes

Reaction equation

HRID 2047495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:38])[C:10]([N:12]([CH3:37])[C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:16][N:15]([C:25]([O:27]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:14]2)=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:39][S:40]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)(=[O:42])=[O:41].O>CN1CCCC1=O>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]([CH3:38])[C:10]([N:12]([C@H:13]2[C@H:17]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:16][N:15]([C:25]([N:46]3[CH2:47][CH2:48][N:43]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:44][CH2:45]3)=[O:27])[CH2:14]2)[CH3:37])=[O:11])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7091611-(Methylsulfonyl)piperazineHCID 67232390HCID 67232390, compound

Product 1

HCID 67231452HCID 67231452, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the compound (0.31 g) obtained in Example 419 and 1-(methylsulfonyl)piperazine (0.14 g) in 1-methyl-2-pyrrolidone (5 mL) was stirred at 110° C. for 24 hr and at 135° C. for 14 hr. The reaction mixture was poured into water, and extracted twice with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 75→100% ethyl acetate/hexane) to give the title compound (0.16 g, 48%) as a pale-yellow powder.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 75→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23e40220e906471fb1520ba40d5041de
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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