Hydrochloric Acid → HCID 59571072, compound

HRID 2192949Notes

Reaction equation

HRID 2192949 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH2:26][CH2:27][O:28]C4CCCCO4)=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.Cl.O>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH2:26][CH2:27][OH:28])=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:11])=[O:12])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59570969HCID 59570969, compound

Product 1

HCID 59571072HCID 59571072, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)-N-{5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-yl}propanamide (118 mg) in THF (10 mL) was added 1 M hydrochloric acid (10 mL) at room temperature, followed by stirring for 2 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After concentration, the obtained crude product was purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1) to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-[5-(2-hydroxyethyl)pyrazin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (94 mg) as a white amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe obtained crude product
  6. customwas purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-65b56eec76894a22abdf5e6081886efb
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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