Cyclopropanesulfonyl chloride → HCID 178527448, compound

HRID 1969870Notes

Reaction equation

HRID 1969870 reaction equation
[C:1]1([C:13]23[CH2:20][CH2:19][C:16]([NH2:21])([CH2:17][CH2:18]2)[CH2:15][CH2:14]3)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][N:2]=1.[CH:22]1([S:25](Cl)(=[O:27])=[O:26])[CH2:24][CH2:23]1>CN(C=O)C.O>[C:1]1([C:13]23[CH2:20][CH2:19][C:16]([NH:21][S:25]([CH:22]4[CH2:24][CH2:23]4)(=[O:27])=[O:26])([CH2:17][CH2:18]2)[CH2:15][CH2:14]3)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][N:2]=1

Participants

5

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride2×HCID 178507109HCID 178507109, compound

Product 1

HCID 178527448HCID 178527448, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)bicyclo[2.2.2]octan-1-amine (0.075 g, 0.267 mmol) in DMF (2.5 mL) was added TEA (0.06 mL, 0.40 mmol) and cyclopropanesulfonyl chloride (0.027 mL, 0.27 mmol, Matrix). The reaction mixture was stirred at ambient temperature for about 16 h. Cyclopropanesulfonyl chloride (0.014 mL, 0.133 mmol, Matrix) was added to the reaction mixture and the reaction continued to stir at ambient temperature for about 4 h. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concd under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to give N-(4-(3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide (0.015 g, 15%) as a white solid: LC/MS (Table 1, Method b) Rt=1.72 min; MS m/z: 386 (M+H)+.

Workup

  1. stirringto stir at ambient temperature for about 4 h
  2. extractionextracted with DCM (3×10 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-4ee83db274e94718bfdcd2579cc94d00
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…