Stannous Chloride → HCID 131732294, compound

HRID 1424842Notes

Reaction equation

HRID 1424842 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[C:31]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[Sn](Cl)Cl>CCO.C(OCC)(=O)C>[NH2:35][C:32]1[CH:33]=[CH:34][C:29]([N:24]([C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:23][C:8]3[C:9]([C:19]([NH:21][CH3:22])=[O:20])=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=4)[O:11][C:7]=3[CH:6]=2)[S:25]([CH3:28])(=[O:26])=[O:27])=[CH:30][C:31]=1[S:38]([CH3:41])(=[O:40])=[O:39]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 131732295HCID 131732295, compound

Product 1

HCID 131732294HCID 131732294, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(3-(methylsulfonyl)-4-nitrophenyl)methylsulfonamido)benzofuran-3-carboxamide (0.7 g, 1.164 mmol) in 1:1 EtOH/Ethyl acetate (10 mL) was added tin(II) chloride (1.324 g, 6.98 mmol). The reaction was heated at 70° C. for 3 h. Solvent was evaporated and the reaction was partitioned between EtOAc and water. The resulting semi viscous mass was filtered (6 h) and the solid obtained (0.5 g, 75%) was progressed as is to the next step. LCMS (m/z, ES+)=572 (M+H+).

Workup

  1. customSolvent was evaporated
  2. customthe reaction was partitioned between EtOAc and water
  3. filtrationThe resulting semi viscous mass was filtered (6 h)
  4. customthe solid obtained (0.5 g, 75%)

Sources & evidence

ORD record
ord-e6f1ebc7cd95438fa10f1da219ad1f2c
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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