Chloride → HCID 14390323, compound

HRID 2351708Notes

Reaction equation

HRID 2351708 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:17]([CH2:18][C:19]([N:23]([CH3:22])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 7515N-MethylanilineHCID 8471TriethylamineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390323HCID 14390323, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under nitrogen atmosphere, oxayl chloride (2.21 g, 0.0174 mole) was added slowly dropwise to a stirred and chilled (~10° C.) suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) in 75 ml of dimethylformamide. After the addition was complete, the reaction was heated at 60° C. for 5 hrs. This acylchloride solution was added dropwise to a stirred and cooled (~10° C.) solution of N-methylaniline (2.02 g, 0.019 mole), triethylamine (1.88 g, 0.019 mole), and 74 ml of dimethylformamide. The reaction was stirred at room temperature overnight. The reaction mixture was poured into 200 ml of water and diluted with water until the cloud point. The mixture was seeded and refrigerated overnight. The solid was collected by filtration and dried under high vacuum. The solid was suspended in dilute, sodium bicarbonate, collected by filtration, washed with water, and dried under high vacuum at 50° C. The solid was recrystallized from isopropyl alcohol-water, collected by filtration, washed with water, and dried under high vacuum first at 56° C., then at 98° C. for 2 days to give 3.0 g (45%) of crystals, mp 170°-171° C.

Workup

  1. temperaturechilled
  2. additionAfter the addition
  3. stirringa stirred
  4. stirringThe reaction was stirred at room temperature overnight
  5. filtrationThe solid was collected by filtration
  6. customdried under high vacuum
  7. additionin dilute
  8. filtrationsodium bicarbonate, collected by filtration
  9. washwashed with water
  10. customdried under high vacuum at 50° C
  11. customThe solid was recrystallized from isopropyl alcohol-water
  12. filtrationcollected by filtration
  13. washwashed with water
  14. customdried under high vacuum first at 56° C.

Sources & evidence

ORD record
ord-cbbbadc225284bf68a1455b3b10d4d9c
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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