Hydrochloric Acid → HCID 58382164, compound

HRID 1628098Notes

Reaction equation

HRID 1628098 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C: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)=N)=[CH:5][CH:4]=1.Cl.C1C[O:34]CC1>>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C: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)=[O:34])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58382201HCID 58382201, compound

Product 1

HCID 58382164HCID 58382164, compoundYield 75%

Procedure

(4-(Methylthio)phenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanimine (1.00 g, 2.37 mmol, prepared using AF from Preparation #AE.1 with (4-(methylthio)phenyl)magnesium bromide) was dissolved in THF (25 mL) then 6 N HCl (1.18 mL, 7.10 mmol) was added. The mixture was stirred rt for about 1 h then concentrated under reduced pressure. Saturated aqueous NaHCO3 (40 mL) and water (10 mL) were added then the mixture was extracted with DCM (50 mL and 15 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give (4-(methylthio)phenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanone (0.754 g, 75%): LC/MS (Table 2, Method b) Rt=2.77 min; MS m/z 424 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionSaturated aqueous NaHCO3 (40 mL) and water (10 mL) were added
  3. extractionthe mixture was extracted with DCM (50 mL and 15 mL)
  4. dry with materialThe combined organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65ab36678a2a4967b7f2f55a485dad9e
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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