Triethylamine → (R)-N-[1-{N-(2-chlorophenethyl)-2-nitrophenylsulfonamido}propan-2-yl]isoquinoline-6-sulfonamide

HRID 333999Notes

Reaction equation

HRID 333999 reaction equation
C(N(CC)CC)C.[NH2:8][C@H:9]([CH3:33])[CH2:10][N:11]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13].[CH:34]1[C:43]2[C:38](=[CH:39][C:40]([S:44](Cl)(=[O:46])=[O:45])=[CH:41][CH:42]=2)[CH:37]=[CH:36][N:35]=1>ClCCl>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][CH2:24][N:11]([CH2:10][C@H:9]([NH:8][S:44]([C:40]1[CH:39]=[C:38]2[C:43](=[CH:42][CH:41]=1)[CH:34]=[N:35][CH:36]=[CH:37]2)(=[O:45])=[O:46])[CH3:33])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55280287Isoquinoline-6-sulfonyl chlorideHCID 86699360(R)-N-(2-aminopropyl)-N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 86699365(R)-N-[1-{N-(2-chlorophenethyl)-2-nitrophenylsulfonamido}propan-2-yl]isoquinoline-6-sulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3 mL of triethylamine and 280 mg of (R)—N-(2-aminopropyl)-N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide prepared in Reference Example 6 were added with stirring at room temperature to a dichloromethane solution of isoquinoline-6-sulfonyl chloride prepared in Reference Example 1, and the mixture was then stirred for 6 hours. The reaction solution was washed with saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to obtain 300 mg of the title compound (73%).

Workup

  1. additionwere added
  2. customprepared in Reference Example 1
  3. washThe reaction solution was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-63510e7559d743309916e013a9c2d2f8
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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