Hydrochloric Acid → HCID 131729710, compound

HRID 1922307Notes

Reaction equation

HRID 1922307 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.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=1.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.[ClH:60]>ClCCl.CO>[ClH:60].[CH3:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11228788(6-Methylpyridin-3-yl)methanolHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 131729710HCID 131729710, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (700 mg, 2.74 mmol, Description 3) and (6-methyl-3-pyridinyl)methanol (338 mg, 2.74 mmol) in dichloromethane (30 ml) was stirred under argon at room temperature, Triphenylphosphine (719 mg, 2.74 mmol) and diisopropyl azodicarboxylate (0.533 ml, 2.74 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. The reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was purified by SCX column eluting with 1 M ammonia in methanol solution and column chromatography on silica using 1 to 99% ethyl acetate in n-pentane to give a white solid. The free base solid was dissolved in methanol and treated with ethereal hydrochloride to give the title compound (554 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature under argon for 16 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe desired product was purified by SCX column
  7. washeluting with 1 M ammonia in methanol solution and column chromatography on silica using 1 to 99% ethyl acetate in n-pentane
  8. customto give a white solid

Sources & evidence

ORD record
ord-0bf846c3eebf499d8ea2fc7422aec7c2
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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