Water → HCID 59427348, compound

HRID 1042906Notes

Reaction equation

HRID 1042906 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[S:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:24][N:23]=2)=[CH:17][CH:16]=1)([O-])=O.[Sn](Cl)Cl.O>CN(C=O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[S:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:24][N:23]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 67316847HCID 67316847, compound

Product 1

HCID 59427348HCID 59427348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-(6-nitroquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine (228 mg, 455 μmol) in 1 mL of DMF, was added tin (II) chloride (431 mg, 2273 μmol) and 115 uL of water. After 15 minutes of sonication, the reaction was stirred at rt. After 2 days, water was removed under vacuum azeotropically with benzene. DCM was added to the suspension. Yellow solids precipitated out of the solution and were filtered off with DCM. The filtrate was concentrated and purified by RPLC on an acidic Gilson column system. Fractions containing the product were washed with sat. NaHCO3. The product was extracted with DCM. The organic was washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified further by performing a column chromatography using 60:40 DCM:(90:10:1 DCM:MeOH:NH4OH). Yellow solid, N-(4-(6-aminoquinolin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine was obtained.

Workup

  1. customAfter 15 minutes of sonication
  2. customwater was removed under vacuum azeotropically with benzene
  3. additionDCM was added to the suspension
  4. customYellow solids precipitated out of the solution
  5. filtrationwere filtered off with DCM
  6. concentrationThe filtrate was concentrated
  7. custompurified by RPLC on an acidic Gilson column system
  8. additionFractions containing the product
  9. washwere washed with sat. NaHCO3
  10. extractionThe product was extracted with DCM
  11. washThe organic was washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe product was purified further

Sources & evidence

ORD record
ord-441e5bff938143ee983436cbe5c61689
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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