1,4-Dichloroisoquinoline-7-sulfonyl chloride → HCID 16658292, compound

HRID 2289786Notes

Reaction equation

HRID 2289786 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([NH:17][C:18]3([C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:11][CH:12]=2)[C:7](NC(N)=N)=[N:6][CH:5]=1.Cl.Cl.NC1(C(N2CCN(C)CC2)=O)CCCC1.[Cl:53]C1C2C(=CC=C(S(Cl)(=O)=O)C=2)C(Cl)=CN=1>C(Cl)Cl>[Cl:53][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([S:14]([NH:17][C:18]3([C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]3)(=[O:16])=[O:15])[CH:9]=2)[C:4]([Cl:3])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideHCID 18698213256478-14-5HCID 178481059HCID 178481059, compound

Product 1

HCID 16658292HCID 16658292, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-1-guanidino-N-{1-[(4-methylpiperazino)carbonyl]cyclopentyl}-7-isoquinolinesulphonamide dihydrochloride ##STR90## Triethylamine (1.36 ml, 10.0 mmol) was added to a solution of (1-aminocyclopentyl)(4-methyl-1-piperazinyl)methanone dihydrochloride (567 mg, 2.0 mmol) and 1,4-dichloro-7-isoquinolinesulphonyl chloride (592 mg, 2.0 mmol) in CH2Cl2 (25 ml), and the reaction stirred at room temperature for 18 h. The mixture was concentrated in vacuo and the residue partitioned between EtOAc and water, and the layers separated. The organic phase was washed with water, extracted with HCl (2N), and these combined acidic extracts washed with EtOAc, and re-basified using Na2CO3. This aqueous solution was extracted with EtOAc, the combined organic extracts washed with brine, dried (Na2SO4) and evaporated in vacuo to give a foam. This was crystallised from CH2Cl2 -i-Pr2O to afford 1,4-dichloro-N-{1-[(4-methyl-1-piperazinyl)carbonyl]cyclopentyl}-7-isoquinolinesulphonamide (153 mg, 0.33 mmol) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and water
  3. customthe layers separated
  4. washThe organic phase was washed with water
  5. extractionextracted with HCl (2N)
  6. washthese combined acidic extracts washed with EtOAc
  7. extractionThis aqueous solution was extracted with EtOAc
  8. washthe combined organic extracts washed with brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo
  11. customto give a foam
  12. customThis was crystallised from CH2Cl2 -i-Pr2O

Sources & evidence

ORD record
ord-b2b807a312bd4a318a32ca6a1907c48e
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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