1,4-Dioxa-8-azaspiro(4.5)decane → HCID 21064665, compound

HRID 1243794Notes

Reaction equation

HRID 1243794 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7](OS(C(F)(F)F)(=O)=O)=[CH:8][C:9]=2[S:11]([CH3:13])=[O:12])[S:4][C:3]=1[C:22](=[O:24])[NH2:23].[O:25]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[O:28][CH2:27][CH2:26]1>CN(C=O)C.O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:32]3[CH2:33][CH2:34][C:29]4([O:28][CH2:27][CH2:26][O:25]4)[CH2:30][CH2:31]3)=[CH:8][C:9]=2[S:11]([CH3:13])=[O:12])[S:4][C:3]=1[C:22]([NH2:23])=[O:24]

Participants

5

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 23401026HCID 23401026, compound

Product 1

HCID 21064665HCID 21064665, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 3-amino-2-carbamoyl-4-methanesulfinyl-thieno[2,3-b]pyridin-6-yl ester (3.00 g, 7.44 mmol) in DMF (100 mL) was added 1,4-dioxa-8-azaspiro[4,5]-decane (2.20 g, 15.4 mmol). The mixture was heated to 70° C. for 1 h. The mixture was cooled to room temperature, diluted with H2O, and washed with CH2Cl2. The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 1.25 g (42.2%) of 3-amino-6-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methanesulfinyl-thieno[2,3-b]pyridine-2-carboxylic acid amide as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with CH2Cl2
  3. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f965c103dce84d529d9bef1c2d566d2a
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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