tert-Butylsulfinamide, (S)-(-)- → HCID 58557252, compound

HRID 1969569Notes

Reaction equation

HRID 1969569 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=O)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:22][C:23]([S@@:26]([NH2:28])=[O:27])([CH3:25])[CH3:24]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:22][C:23]([S@@:26](/[N:28]=[CH:20]/[C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:15]2=[N:16][CH:17]=1)=[O:27])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

Product 1

HCID 58557252HCID 58557252, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (8.66 g, 28.7 mmol, Preparation #12 Step B) and (S)-2-methylpropane-2-sulfinamide (4.18 g, 34.5 mmol) in DCM (20 mL) at ambient temperature was added anhydrous powdered copper(II) sulfate (13.8 g, 86 mmol). After about 20 h, the reaction mixture was filtered and partially concd in vacuo. Heptane was added to the solution and the resulting solids were collected by filtration and dried in vacuo to provide (S,E)-2-methyl-N-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylene)propane-2-sulfinamide (11.5 g, 99%) as a solid. LC/MS (Table 1, Method a) Rt=2.50 min; MS m/z: 405 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered and partially concd in vacuo
  2. additionHeptane was added to the solution
  3. filtrationthe resulting solids were collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-33518e29bad94c719e009d927fc7b45a
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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