Dimethyl Sulfoxide → HCID 66742261, compound

HRID 449595Notes

Reaction equation

HRID 449595 reaction equation
[CH2:1]1[C:4]2([CH2:7][NH:6][CH2:5]2)[CH2:3][N:2]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Br[C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=1.CS(C)=O>O>[C:11]([O:10][C:8]([N:2]1[CH2:3][C:4]2([CH2:7][N:6]([C:16]3[CH:21]=[N:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:5]2)[CH2:1]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8176205-Bromo-2-nitropyridineHCID 401519812-Boc-2,6-diazaspiro(3.3)heptane

Product 1

HCID 66742261HCID 66742261, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a 25 mL pear-shaped flask, tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate (2.81 g, 14.2 mmol), 5-bromo-2-nitropyridine (2.88 g, 14.2 mmol), and TEA (1.58 g, 2.17 ml, 15.6 mmol) were combined with DMSO (12 ml) to give a light yellow solution. The reaction mixture was heated to 90° C. and stirred for 40 h. Cooled to 25° C. and the reaction mixture was diluted with 50 mL H2O and extracted with EtOAc (3×50 mL). The organic layers were combined, washed with sat NaCl (1×50 mL), dried over Na2SO4 and concentrated in vacuo. The purple oil was used crude in the subsequent reduction. (M+H)+=321 m/e.

Workup

  1. customto give a light yellow solution
  2. temperatureCooled to 25° C.
  3. extractionextracted with EtOAc (3×50 mL)
  4. washwashed with sat NaCl (1×50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ca5f8ec64e742c58d30ed432087b6d0
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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