Piconol → N-{(2S)-5-[(2-pyridinylmethyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

HRID 1922299Notes

Reaction equation

HRID 1922299 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2

Participants

6

Reactant 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 44124831N-{(2S)-5-[(2-pyridinylmethyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.39 mmol, Description 3) and 2-pyridinylmethanol (43 mg, 0.39 mmol) in dichloromethane (3 ml), was treated with triphenylphosphine (103 mg, 0.39 mmol) and then diisopropyl azodicarboxylate (77 ul, 0.39 mmol). The resulting solution was stirred at room temperature, under an atmosphere of argon, for 16 hours. The solution was then partitioned between water and dichloromethane and the organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP. The resulting solution was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to obtain the title compound as a white solid (70 mg).

Workup

  1. customThe solution was then partitioned between water and dichloromethane
  2. dry with materialthe organic solution was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto yield the crude product
  5. customThe crude product was purified
  6. additionThe resulting solution was diluted with saturated aqueous sodium bicarbonate solution
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5706f29940e842ca90caf26f021259fd
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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