Stannous Chloride → HCID 178482254, compound

HRID 1189670Notes

Reaction equation

HRID 1189670 reaction equation
[F:1][C:2]([F:34])([F:33])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:31])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:5][CH2:4]1.Cl[Sn]Cl>CCOC(C)=O>[F:34][C:2]([F:1])([F:33])[C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[C:15]([NH2:17])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:31])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 178482255HCID 178482255, compound

Product 1

HCID 178482254HCID 178482254, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-[N-methyl-N-(4-fluorobenzyl)amino]-4-methylamino-5-nitro-benzoic acid amide (80 mg, 0.166 mmol), SnCl2 (183 mg 0.81 mmol) and 5 mL EtOAc is stirred at reflux for 1 h. The mixture is filtered through a pad of celite and the celite pad is washed with EtOAc. The combined organic phases are dried with Na2SO4, filtered and concentrated. Yield: 68 mg. HPLC Rt=1.35 min (method A). MS m/z: 453 [M+H]+.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationThe mixture is filtered through a pad of celite
  3. washthe celite pad is washed with EtOAc
  4. dry with materialThe combined organic phases are dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ab60f1b556e4846a4c8a087c264c9c0
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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