Triethylamine → HCID 14390286, compound

HRID 621942Notes

Reaction equation

HRID 621942 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][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.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=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

7

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 65578Oxalyl chlorideHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390286HCID 14390286, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (1.73 g, 0.014 mole) was added slowly to a stirred and chilled (10°-15° C.) suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.7 g, 0.013 mole) in 50 ml of dry dimethylformamide. The reaction mixture was heated between 60°-90° C. for 5 hours. The solution of the acyl chloride was added dropwise under a nitrogen atmosphere to a stirred, chilled (10°-15° C.) solution of 2-aminopyridine (1.77 g, 0.019 mole), and triethylamine (1.90 g, 0.019 mole) in 75 ml of dry dimethylformamide. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water, diluted with water to the cloud point, and seeded. The crystalline solid was collected by filtration, washed with water, and dried under high vacuum at 70° C. for 2 hours, then at 60° C. overnight togive 1.0 g (20%) of crystals, mp 190°-191° C.

Workup

  1. temperaturechilled
  2. temperatureThe reaction mixture was heated between 60°-90° C. for 5 hours
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. filtrationThe crystalline solid was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum at 70° C. for 2 hours
  7. customat 60° C.
  8. customovernight togive 1.0 g (20%) of crystals, mp 190°-191° C.

Sources & evidence

ORD record
ord-1975afed26dd4a9895d39957d978efa0
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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