4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 66882740, compound

HRID 390314Notes

Reaction equation

HRID 390314 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([O:9][CH:10]2[CH2:14][CH2:13][N:12]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:11]2)[N:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>N1C=CC=CC=1.ClCCl.[OH-].[Na+]>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([O:9][CH:10]3[CH2:14][CH2:13][N:12]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:11]3)=[CH:5][CH:6]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 668834292-Methyl-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridin-3-amine

Product 1

HCID 66882740HCID 66882740, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Methyl-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridin-3-amine (340 mg) was dissolved in pyridine (3.3 mL) and 4-isopropylbenzenesulfonyl chloride (358 mg) was slowly added under stirring. After 19 h stirring at room temperature, the reaction mixture was diluted with dichloromethane and 2 M aqueous NaOH was added. After stirring for 1 h at room temperature the phases were separated. The organic phase was dried (sodium sulfate), concentrated and the crude product purified by flash chromatography (silica, dichloromethane, 0.5 to 5% methanol gradient). Yield: 460 mg (78%, pale yellow oil).

Workup

  1. stirringAfter 19 h stirring at room temperature
  2. additionwas added
  3. stirringAfter stirring for 1 h at room temperature the phases
  4. customwere separated
  5. dry with materialThe organic phase was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customthe crude product purified by flash chromatography (silica, dichloromethane, 0.5 to 5% methanol gradient)

Sources & evidence

ORD record
ord-9d4ec63043de4c9d83611293ee33e0fd
Source dataset
uspto-grants-2013_02
Patent number
US08383641B2

Reaction notes

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