Stannous Chloride → HCID 178482256, compound

HRID 1189673Notes

Reaction equation

HRID 1189673 reaction equation
[F:1][C:2]([F:29])([F:28])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:26])[CH2:23][C:24]#[N:25])[CH2:5][CH2:4]1.Cl[Sn]Cl>CCOC(C)=O>[F:1][C:2]([F:28])([F:29])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([NH2:17])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:26])[CH2:23][C:24]#[N:25])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 178482257HCID 178482257, compound

Product 1

HCID 178482256HCID 178482256, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-[N-methyl-N-cyanomethyl-amino]-4-methylamino-5-nitro-benzoic acid amide (50 mg, 0.12 mmol), SnCl2 (134 mg 0.59 mmol and 5 mL EtOAc is stirred at reflux for 4 h. The mixture is diluted with EtOAc, washed with sat aq NaHCO3, 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.

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with sat aq NaHCO3
  3. filtrationfiltered through a pad of celite
  4. washthe celite pad is washed with EtOAc
  5. dry with materialThe combined organic phases are dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1d71812215d46a7b0880284f09eb468
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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