Water → (R)-N-{1-(2-chlorophenethylamino)propan-2-yl}isoquinoline-6-sulfonamide

HRID 334000Notes

Reaction equation

HRID 334000 reaction equation
C1(S)C=CC=CC=1.[Cl:8][C:9]1[CH:46]=[CH:45][CH:44]=[CH:43][C:10]=1[CH2:11][CH2:12][N:13]([CH2:26][C@H:27]([NH:29][S:30]([C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[CH:39]=[N:38][CH:37]=[CH:36]2)(=[O:32])=[O:31])[CH3:28])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:8][C:9]1[CH:46]=[CH:45][CH:44]=[CH:43][C:10]=1[CH2:11][CH2:12][NH:13][CH2:26][C@H:27]([NH:29][S:30]([C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[CH:39]=[N:38][CH:37]=[CH:36]2)(=[O:32])=[O:31])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 86699365(R)-N-[1-{N-(2-chlorophenethyl)-2-nitrophenylsulfonamido}propan-2-yl]isoquinoline-6-sulfonamide

Product 1

HCID 86699366(R)-N-{1-(2-chlorophenethylamino)propan-2-yl}isoquinoline-6-sulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.1 mL of thiophenol was added to a suspension of 300 mg of (R)—N-[1-{N-(2-chlorophenethyl)-2-nitrophenylsulfonamido}propan-2-yl]isoquinoline-6-sulfonamide and 360 mg of potassium carbonate in 20 mL of acetonitrile, and the mixture was stirred at room temperature for 16 hours. 50 mL of water was added to the reaction solution, followed by extraction with ethyl acetate (50 mL×2). The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 179 mg of the title compound as a white solid (87%).

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 mL×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-097e83dac5f841f2ac40071b1367f370
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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