Hydrochloric Acid → HCID 131729709, compound

HRID 1922305Notes

Reaction equation

HRID 1922305 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][C@H:14]([NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH2:13]3)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:26]>CO>[ClH:26].[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[CH2:15][C@H:14]([NH:19][S:20]([CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:22])[CH2:13]3)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44124832HCID 44124832, compound

Product 1

HCID 131729709HCID 131729709, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-((2S)-5-{[(2-methyl-3-pyridinyl)methyl]oxy}-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide (free base, 6.5 g, 18.03 mmol) in dry methanol (65 mL) at 0° C. under argon, hydrochloric acid (1M in Et2O, 21.64 mL, 21.64 mmol) was added dropwise. The mixture was stirred at 0° C. for 10 minutes then at room temperature for 30 minutes. Volatiles were evaporated under reduced pressure and the resulting solid residue was triturated with Et2O/pentane 40 ml/30 ml. The product was collected by filtration washing the cake with pentane (30 ml) and drying the material at high vacuum to get the title compound (6.95 g) as a white solid.

Workup

  1. waitat room temperature for 30 minutes
  2. customVolatiles were evaporated under reduced pressure
  3. customthe resulting solid residue was triturated with Et2O/pentane 40 ml/30 ml
  4. filtrationThe product was collected by filtration
  5. washwashing the cake with pentane (30 ml)
  6. customdrying the material at high vacuum

Sources & evidence

ORD record
ord-c94bea5148004c8d8efe9fdaac89e74d
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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