Dimethylformamide → HCID 58382318, compound

HRID 1627996Notes

Reaction equation

HRID 1627996 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[NH:5][CH:4]=1)[CH3:2].[H-].[Na+].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].[CH3:28]N(C=O)C>>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]3[CH:14]=[N:13][N:12]([CH3:28])[C:10]3=2)[N:5]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:4]=1)[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178437173HCID 178437173, compound

Product 1

HCID 58382318HCID 58382318, compoundYield 78%

Procedure

8-Ethyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (10.5 g, 56.3 mmol) in DMF (200 mL) was cooled to about 0° C. then treated with 60 wt % NaH (2.36 g, 59.1 mmol). After about 20 min, TsCl (11.3 g, 59.1 mmol) was added in portions. After about 40 min the mixture was poured slowly into ice water (300 mL) and stirred. The solids were collected by filtration then the material was dissolved in DCM (300 mL). The water layer was separated then the organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was triturated with Et2O then the solids were collected by filtration and dried to constant weight to provide 8-ethyl-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (14.8 g, 78%): LC/MS (Table 2, Method c) Rt=1.55 min; MS m/z 355 (M+H)+.

Workup

  1. filtrationThe solids were collected by filtration
  2. dissolutionthe material was dissolved in DCM (300 mL)
  3. customThe water layer was separated
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was triturated with Et2O
  8. filtrationthe solids were collected by filtration
  9. customdried to constant weight

Sources & evidence

ORD record
ord-263a5c699647412f821dd86f18f16cdd
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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