Hydrochloric Acid → HCID 67403895, compound

HRID 407100Notes

Reaction equation

HRID 407100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]([F:26])([F:25])[F:24])=[N:19][NH:20][C:21]=3[CH3:22])=[C:13]([N+:27]([O-])=O)[CH:12]=2)=[O:9])=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl>CCO>[NH2:27][C:13]1[CH:12]=[C:11]([NH:10][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:9])[CH:16]=[CH:15][C:14]=1[C:17]1[C:18]([C:23]([F:26])([F:24])[F:25])=[N:19][NH:20][C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 131731631HCID 131731631, compound

Product 1

HCID 67403895HCID 67403895, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 23 (340 mg, 1.24 mmol), SnCl2 2H2O (902 mg, 6.22 mmol), HCl (0.33 mL) in EtOH (50 mL) stirred at reflux under a N2 atmosphere for 1 h. The solvent was removed under vacuo, washed with NaOH to PH=14, extracted with CH2Cl2, dried over Na2SO4 and purified by column chromatography to give 24 (235 mg, 75% yield). 1H NMR (CDCl3, 300 MHz): δ=2.37 (s, 3H), 3.89 (s, 2H), 6.59 (s, 1H), 6.76-6.79 (m, 1H), 7.13 (d, 1H), 7.46-7.49 (m, 2H), 7.53 (d, 1H), 7.73 (s, 1H), 7.79-7.81 (m, 2H). LC-MS: 394.9 (M+1)+.

Workup

  1. temperatureat reflux under a N2 atmosphere for 1 h
  2. customThe solvent was removed under vacuo
  3. washwashed with NaOH to PH=14
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-c3a005d7a73e4944afc99898087fe7a3
Source dataset
uspto-grants-2014_06
Patent number
US08754219B2

Reaction notes

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