Oxalyl chloride → HCID 71267437, compound

HRID 1505795Notes

Reaction equation

HRID 1505795 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=O.[Cl:7][C:8]1[NH:12][C:11]2[CH:13]=[C:14]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])=[O:22])[CH:15]=[C:16]([C:17]([OH:19])=O)[C:10]=2[N:9]=1>C1COCC1.CN(C=O)C>[Cl:7][C:8]1[NH:12][C:11]2[CH:13]=[C:14]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])=[O:22])[CH:15]=[C:16]([C:17]([NH:9][C:10]3[CH:11]=[CH:13][CH:2]=[C:1]([Cl:6])[C:16]=3[CH3:15])=[O:19])[C:10]=2[N:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 90229438HCID 90229438, compound

Product 1

HCID 71267437HCID 71267437, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (1.42 mL) was added dropwise to a stirring solution of 2-chloro-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid (1.27 g) in THF (13 mL) under ice-cooling. To the mixture was added DMF (five drops), and it was stirred at room temperature for 2 hours. From the reaction mixture was removed the solvent and excessive oxalyl chloride under reduced pressure. To the residue was added toluene, and it was concentrated under reduced pressure, dried, and then dissolved in THF (10 mL). The solution was dropped slowly to a solution of 3-chloro-2-methylaniline (0.42 mL) and N,N-diisopropylethylamine (2.3 mL) in THF (10 mL) under ice-cooling for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (0.58 g) as white powder.

Workup

  1. temperaturecooling
  2. customFrom the reaction mixture was removed the solvent and excessive oxalyl chloride under reduced pressure
  3. additionTo the residue was added toluene, and it
  4. concentrationwas concentrated under reduced pressure
  5. customdried
  6. dissolutiondissolved in THF (10 mL)
  7. additionThe solution was dropped slowly to a solution of 3-chloro-2-methylaniline (0.42 mL) and N,N-diisopropylethylamine (2.3 mL) in THF (10 mL) under ice-
  8. temperaturecooling for 1 hour
  9. additionThe reaction mixture was diluted with ethyl acetate
  10. washwashed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-4def01491ccd48d5a448ead80e1fca3d
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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