Triethylamine → HCID 70356980, compound

HRID 623106Notes

Reaction equation

HRID 623106 reaction equation
C(Cl)(=O)C([Cl:4])=[O:3].[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.Cl.Cl.[CH3:30][N:31]([CH3:39])[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.C(N(CC)CC)C>CN(C)C=O>[OH2:3].[ClH:4].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([C@@H:23]([CH3:27])[C:24]([NH:38][C:35]3[CH:36]=[CH:37][C:32]([N:31]([CH3:39])[CH3:30])=[CH:33][CH:34]=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 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 27241661,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 14390427(S)-2-(4-chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 70356980HCID 70356980, compoundYield 443.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.41 g, 0.019 mole) was added dropwise, slowly, 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 anhydrous dimethylformamide (75 ml). The suspension was stirred at room temperature for 30 minutes and then an additional portion of oxalyl chloride (0.73 g, 0.0057 mole) was added. The resulting solution was stirred at room temperature for 45 minutes and then added slowly to a suspension of N,N-dimethyl-1,4-benzenediamine dihydrochloride (3.97 g, 0.0019 mole) and triethylamine (7.7 g, 0.076 mole) in anhydrous dimethylformamide (150 ml). The reaction mixture was stirred at room temperature overnight under nitrogen and protected from light. The solution was then poured into 400 ml of ice water. The resulting solid was collected by filtration, rinsed with water, dissolved in hot isopropyl alcohol, filtered, and cooled to room temperature. Upon addition of water, solid precipitated. The solid was collected by filtration, dissolved in hot tetrahydrofuran, and made acidic with ethereal hydrogen chloride. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at 50° C. to give 4.0 g (47%) of title compound, mp 186°-190° C.

Workup

  1. temperaturechilled
  2. stirringThe suspension was stirred at room temperature for 30 minutes
  3. stirringThe resulting solution was stirred at room temperature for 45 minutes
  4. stirringThe reaction mixture was stirred at room temperature overnight under nitrogen
  5. filtrationThe resulting solid was collected by filtration
  6. washrinsed with water
  7. dissolutiondissolved in hot isopropyl alcohol
  8. filtrationfiltered
  9. additionUpon addition of water, solid
  10. customprecipitated
  11. filtrationThe solid was collected by filtration
  12. dissolutiondissolved in hot tetrahydrofuran
  13. filtrationThe solid was collected by filtration
  14. washrinsed with isopropyl ether
  15. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-e953fee45a6841bea33fa33bb7f90732
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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