Triethylamine → 2-(3-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride

HRID 2072990Notes

Reaction equation

HRID 2072990 reaction equation
C(Cl)(=O)C([Cl:4])=O.[Cl:7][C:8]1[CH:9]=[C:10]([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:11]=[CH:12][CH:13]=1.Cl.Cl.[CH3:29][N:30]([CH3:38])[C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.C(N(CC)CC)C>CN(C)C=O>[ClH:4].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:22]([CH2:23][C:24]([NH:37][C:34]3[CH:35]=[CH:36][C:31]([N:30]([CH3:38])[CH3:29])=[CH:32][CH:33]=3)=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27241661,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143902562-(3-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochlorideYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.8 ml, 0.032 mole) was added dropwise (slowly) to a stirred and chilled solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (8.0 g, 0.028 mole) in anhydrous dimethylformamide (100 ml). The reaction was heated at 55°-60° C. for 3 hrs, cooled to room temperature, and added dropwise to a stirred and chilled (5°-10° C.) suspension of N,N-dimethyl-p-phenylenediamine dihydrochloride (6.7 g, 0.032 mole) and triethylamine (12.9 g, 0.128 mole) in anhydrous dimethylformamide (200 ml). The reaction was stirred at room temperature over the weekend, filtered, and poured into ice water (600 ml). The mixture was filtered and the filter cake recrystallized from ethanol giving 6.6 g (58%). The solid was converted to the hydrochloride salt in isopropyl alcohol and concentrated hydrochloric acid to give 6.6 g of a white granular solid, mp. 229°-231° C. with decomposition.

Workup

  1. temperatureThe reaction was heated at 55°-60° C. for 3 hrs
  2. additionadded dropwise to
  3. stirringa stirred
  4. temperaturechilled
  5. stirringThe reaction was stirred at room temperature over the weekend
  6. filtrationfiltered
  7. additionpoured into ice water (600 ml)
  8. filtrationThe mixture was filtered
  9. customthe filter cake recrystallized from ethanol giving 6.6 g (58%)

Sources & evidence

ORD record
ord-261e0294411d49ba81fe99f8cc288845
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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