tert-Butyl piperazine-1-carboxylate → 6-(4-Tert-butoxycarbonylpiperazin-1-ylsulfonyl)isoquinoline

HRID 1845951

Reaction equation

HRID 1845951 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[S:15]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][CH:22]=[CH:21]2)(=[O:17])=[O:16].NC1C=C2C(=CC=1)C=NC=C2.Cl.Cl.N1(S(C2C=C3C(=CC=2)C=NC=C3)(=O)=O)CCNCC1>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[N:23][CH:22]=[CH:21]3)(=[O:16])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5889916-AminoisoquinolineHCID 55280287Isoquinoline-6-sulfonyl chloride2×HCID 667271316-(Piperazin-1-ylsulfonyl)isoquinoline dihydrochloride

Product 1

HCID 667272096-(4-Tert-butoxycarbonylpiperazin-1-ylsulfonyl)isoquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

0.5 mL of triethylamine and 0.5 g of tert-butoxycarbonylpiperazine were added with stirring at room temperature to a dichloromethane solution (100 mL) of 6-chlorosulfonylisoquinoline (Reference Compound 2) synthesized according to Reference Example 2 from 500 mg of 6-aminoisoquinoline (Reference Compound 1), and reacted for 6 hours. After the completion of reaction, the reaction solution was washed with saturated saline and dried over anhydrous sodium sulfate. After concentration, the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 150 mg of the compound of interest as a white crystal (23%).

Workup

  1. customsynthesized
  2. customreacted for 6 hours
  3. customAfter the completion of reaction
  4. washthe reaction solution was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-8a2892f9f65e4e048d3b0bd54c64f953
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Linked notes

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