N-Methylaniline → HCID 14390413, compound

HRID 2073061Notes

Reaction equation

HRID 2073061 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([C@@H:23]([CH3:27])[C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[CH3:28][NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([C@@H:23]([CH3:27])[C:24]([N:29]([CH3:28])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 14390427(S)-2-(4-chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390413HCID 14390413, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.18 g, 0.0172 mole) was added slowly, dropwise, to a stirred and chilled (10° C.) suspension of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole) in dry dimethylformamide (75 ml). The mixture was stirred at room temperature for 3 hours, heated at 50° C. for one hour and cooled to room temperature. An additional 0.0057 mole of oxalyl chloride was added and the mixture was stirred at room temperature for 30 minutes. N-Methylaniline (1.92 g, 0.0179 mole) was added and the reaction mixture was stirred at room temperature under nitrogen overnight. The mixture was poured into 400 ml of ice water and triethylamine (6 ml) was added. The precipitated solid was collected by filtration, rinsed with water, redissolved in hot isopropyl alcohol, treated with charcoal, filtered hot and allowed to cool. Addition of water caused a solid to form. The solid was collected by filtration, rinsed with water and dried under high vacuum overnight to give 4.2 g (65%) of title compound, mp 174°-177° C.

Workup

  1. temperaturechilled
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. temperaturecooled to room temperature
  4. stirringthe mixture was stirred at room temperature for 30 minutes
  5. stirringthe reaction mixture was stirred at room temperature under nitrogen overnight
  6. additionwas added
  7. filtrationThe precipitated solid was collected by filtration
  8. washrinsed with water
  9. dissolutionredissolved in hot isopropyl alcohol
  10. additiontreated with charcoal
  11. filtrationfiltered hot
  12. temperatureto cool
  13. additionAddition of water
  14. customto form
  15. filtrationThe solid was collected by filtration
  16. washrinsed with water
  17. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-8914e21134cf49ed9074d460c20baaab
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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