Dichloromethane → HCID 131729714, compound

HRID 1922315Notes

Reaction equation

HRID 1922315 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[CH:24]=[C:23]([CH2:25]O)[CH:22]=[CH:21][N: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.[Cl:60]CCl>>[ClH:60].[CH3:18][C:19]1[CH:24]=[C:23]([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:22]=[CH:21][N:20]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 9942144(2-Methylpyridin-4-yl)methanolHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 131729714HCID 131729714, compound

Procedure

A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (200 mg, 0.783 mmol, Description 3) and (2-methyl-4-pyridinyl)methanol (107 mg, 0.783 mmol) in dichloromethane (15 ml) was stirred under argon at room temperature, Triphenylphosphine (205 mg, 0.783 mmol) and diisopropyl azodicarboxylate (0.152 ml, 0.783 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. Solvent was removed by rotary evaporation and the desired product was purified by SCX eluting with 1M ammonia in methanol solution and high pH MDAP to give the title compound as a white solid. The free base solid was dissolved in methanol and treated with ethereal hydrochloride to give the desired compound as a hydrochloride salt (54 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature under argon for 16 hours
  2. customSolvent was removed by rotary evaporation
  3. customthe desired product was purified by SCX
  4. washeluting with 1M ammonia in methanol solution and high pH

Sources & evidence

ORD record
ord-1e3727600a814032a98fb30fcf89a9cc
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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