Triethylamine → HCID 14390313, compound

HRID 2073119Notes

Reaction equation

HRID 2073119 reaction equation
C(Cl)(=O)C(Cl)=O.[Br: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.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>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([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:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27241661,4-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390313HCID 14390313, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.6 g, 0.020 mole) was added dropwise (slowly) to a stirred and chilled (5°-10° C.) suspension of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (6.4 g, 0.019 mole) in anhydrous dimethylformamide (50 ml). The reaction mixture was heated at 55°-60° C. for 5 hours, cooled to room temperature, and added dropwise to a stirred and chilled (10°-15° C.) suspension of N,N-dimethyl-p-phenylenediamine dihydrochloride (4.04 g, 0.0193 mole), triethylamine (8.2 g, 0.081 mole), and anhydrous dimethylformamide (100 ml). The reaction mixture was stirred overnight at room temperature, filtered, and poured into ice water (500 ml). The mixture was allowed to precipitate, and filtered. The filter cake was triturated in potassium bicarbonate solution (100 ml), filtered, and rinsed with water (100 ml). The cake was twice recrystallized from tetrahydrofuran/ethyl alcohol, giving 2.8 g (31%) of a white solid, mp 248°- 250° C.

Workup

  1. temperaturechilled
  2. temperatureThe reaction mixture was heated at 55°-60° C. for 5 hours
  3. additionadded dropwise to
  4. stirringa stirred
  5. temperaturechilled
  6. stirringThe reaction mixture was stirred overnight at room temperature
  7. filtrationfiltered
  8. additionpoured into ice water (500 ml)
  9. customto precipitate
  10. filtrationfiltered
  11. customThe filter cake was triturated in potassium bicarbonate solution (100 ml)
  12. filtrationfiltered
  13. washrinsed with water (100 ml)
  14. customThe cake was twice recrystallized from tetrahydrofuran/ethyl alcohol

Sources & evidence

ORD record
ord-ab1646180c0f4cf9843a355d1666237c
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

Loading…