HCID 55207327, compound → HCID 86616289, compound

HRID 130467Notes

Reaction equation

HRID 130467 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.Cl.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl.N1C=CC=CC=1>[Cl:19][C:20]1[N:25]=[CH:24][C:23]([S:26]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:16][CH3:17])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 55207327HCID 55207327, compoundHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 86616289HCID 86616289, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (587 mg, 2.5 mmol) in dichloromethane (4 ml) and pyridine (4 ml) was treated with a suspension of 6-chloro-3-pyridinesulfonyl chloride hydrochloride (D32) (700 mg, 3 mmol) in dichloromethane (4 ml). After stirring at room temperature for 15 minutes the mixture was evaporated and the residue co-evaporated with toluene (×2). The residue was then partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was separated, washed in water, brine, dried and evaporated. The residue was triturated with ether/and dried to give the title product. MS (ES+) 411/413 [M+H]+.

Workup

  1. customwas evaporated
  2. customThe residue was then partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed in water
  5. dry with materialbrine, dried
  6. customevaporated
  7. customThe residue was triturated with ether/
  8. customdried

Sources & evidence

ORD record
ord-fe994d2f90824d7792da66e3fafb757b
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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