Stannous Chloride → HCID 57703862, compound

HRID 1472213Notes

Reaction equation

HRID 1472213 reaction equation
Cl[Sn]Cl.[CH2:4]([O:6][C:7]([N:9]1[C:13]2[CH2:14][N:15]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:19])=[O:18])[CH2:16][C:12]=2[C:11]([NH:27][C:28](=[O:45])[C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[C:31]([N+:42]([O-])=O)[CH:30]=2)=[N:10]1)=[O:8])[CH3:5]>C(O)C.Cl>[CH2:4]([O:6][C:7]([N:9]1[C:13]2[CH2:14][N:15]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:19])=[O:18])[CH2:16][C:12]=2[C:11]([NH:27][C:28](=[O:45])[C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[C:31]([NH2:42])[CH:30]=2)=[N:10]1)=[O:8])[CH3:5]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 57703875HCID 57703875, compound

Product 1

HCID 57703862HCID 57703862, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

To a solution of 360 mg (1.91 mmol, 5 eq.) of SnCl2 in 3 mL of ethanol at 60° C. were added a solution of 230 mg (0.39 mmol) of 5-(3-fluoro-benzenesulfonyl)-3-[4-(4-methyl-piperazin-1-yl)-3-nitro-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester in 2 mL of ethanol and 2 mL of concentrated hydrochloric acid. After 2 hours, the solvent was removed under reduced pressure, the residue was treated with saturated sodium hydrogencarbonate solution, extracted with ethyl acetate, and the organic phase dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by flash column chromatography, using dichloromethane-methanol 9:1 as eluant, to give 120 mg (54% yield) of 3-[3-amino-4-(4-methyl-piperazin-1-yl)-benzoylamino]-5-(3-fluoro-benzenesulfonyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester as white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was treated with saturated sodium hydrogencarbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-15d0daf921104c739c0b25f81935432f
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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