Tetrahydrofuran → HCID 58382099, compound

HRID 1628096Notes

Reaction equation

HRID 1628096 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:14]3=[N:15][CH:16]=2)[NH2:10])=[CH:5][CH:4]=1.[Br-].[Mg+2].[Br-].[CH2:33]1COCC1.OO[S:40]([O-:42])=[O:41].[K+]>O>[CH3:33][S:40]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=4)(=[O:21])=[O:22])[C:14]3=[N:15][CH:16]=2)[NH2:10])=[CH:7][CH:8]=1)(=[O:42])=[O:41]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 82241Magnesium BromideHCID 23707502Potassium hydroxy sulfiteHCID 58382509HCID 58382509, compound

Product 1

HCID 58382099HCID 58382099, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

In a round flask was added (4-(methylthio)phenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.453 g, 1.067 mmol, prepared using AF from Preparation #AE.1 with 4-(methylthio)phenyl)magnesium bromide and AG) and THF (5 mL) and mixture was cooled to about 0° C. Oxone® (1.312 g, 2.134 mmol) in water (2 mL) was added and the mixture was stirred for about 1 h. The mixture was diluted with water (5 mL) and extracted with DCM (10 mL), dried over MgSO4 and concentrated to provide (4-(methylsulfonyl)phenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.487 g, 100%): LC/MS (Table 2, Method c) Rt=1.25 min; MS m/z 457 (M+H)+.

Workup

  1. extractionextracted with DCM (10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-99b31809322e4d8c9a8e4b33266b5510
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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