Sodium Dithionite → HCID 46244400, compound

HRID 1803850Notes

Reaction equation

HRID 1803850 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:35])[C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH3:25])=[CH:20][C:19]=1[N+:32]([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].O>[NH2:32][C:19]1[CH:20]=[C:21]([N:24]([CH2:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[CH3:25])[CH:22]=[CH:23][C:18]=1[C:17]([NH:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH2:5][C:4]3[CH:3]=[C:2]([F:1])[CH:38]=[C:37]([F:39])[CH:36]=3)[CH:8]=2)[NH:12][N:11]=1)=[O:35]

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 46244493HCID 46244493, compound

Product 1

HCID 46244400HCID 46244400, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-[5-(3,5-Difluoro-benzyloxy)-1H-indazol-3-yl]-4-[(3-dimethylamino-propyl)-methyl-amino]-2-nitro-benzamide (424 mg, 0.79 mmol) in DCM (5 mL) was treated with nBu4NCl (149 mg, 0.54 mmol). Na2S2O4 (969 mg, 4.73 mmol) in water (5 mL) was added drop-wise, with stirring. After 1 hour, the volatiles were removed by evaporation, the residue was taken twice in water, filtered and treated with 4N HCl in dioxane (12 mL). The volatile components were removed by evaporation. The solid was dissolved in DCM (100 mL), washed with saturated NaHCO3 solution and brine. After drying over sodium sulfate and removal of the solvent, the crude was purified over silica gel (DCM: NH3 7N in MeOH 9:1) to afford 260 mg of title compound in 65% yield.

Workup

  1. customthe volatiles were removed by evaporation
  2. filtrationfiltered
  3. additiontreated with 4N HCl in dioxane (12 mL)
  4. customThe volatile components were removed by evaporation
  5. dissolutionThe solid was dissolved in DCM (100 mL)
  6. washwashed with saturated NaHCO3 solution and brine
  7. dry with materialAfter drying over sodium sulfate and removal of the solvent
  8. customthe crude was purified over silica gel (DCM: NH3 7N in MeOH 9:1)

Sources & evidence

ORD record
ord-c8fbdbb9100249ba9fc42366e5f2b748
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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