Triethylamine hydrochloride → HCID 178439909, compound

HRID 488010Notes

Reaction equation

HRID 488010 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]3[N:18]=[C:17]2[CH2:26][CH2:27][CH3:28])=[CH:11][CH:10]=1)#[N:2].[N-:29]=[N+:30]=[N-:31].[Na+].Cl.C(N(CC)CC)C.[OH-].[Na+]>CN1CCCC1=O.C(O)(=O)C.C(OCC)(=O)C>[CH3:25][C:24]1[CH:23]=[CH:22][N:21]=[C:20]2[N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]4[NH:31][N:30]=[N:29][N:2]=4)=[CH:10][CH:11]=3)[C:17]([CH2:26][CH2:27][CH3:28])=[N:18][C:19]=12

Participants

8

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 15288824HCID 15288824, compound

Product 1

HCID 178439909HCID 178439909, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5.3 g of 3-[(2'-cyanobiphenyl-4-yl)methyl]-7-methyl-2-n-propyl-3H-imidazo[4,5-b]pyridine, 5.85 g of sodium azide and 6.19 g of triethylamine hydrochloride were heated in 120 ml of N-methylpyrrolidone as a reaction solvent at an internal temperature of 138° C. for 8 hr under stirring. After cooling, a dilute aqueous sodium hydroxide solution and ethyl acetate were added thereto to cause phase separation, thus obtaining a watery phase. The watery phase was weakly acidified with acetic acid and extracted thrice with ethyl acetate, and the extract was washed four times with water. Methanol was added to the washed extract to dissolve the precipitated crystal in the organic phase, and the organic phase was dried over anhydrous magnesium sulfate. The dried organic phase was concentrated, and the residue was subjected to silica gel chromatography (chloroform:ethanol:acetic acid=97:3:0.2). A fraction of the intended title compound was concentrated and recrystallized from ethanol. The yield was 4.6 g. The melting point was 200° to 202° C.

Workup

  1. temperatureAfter cooling
  2. customphase separation
  3. customthus obtaining a watery phase
  4. extractionextracted thrice with ethyl acetate
  5. washthe extract was washed four times with water
  6. additionMethanol was added to the washed
  7. extractionextract
  8. dissolutionto dissolve the precipitated crystal in the organic phase
  9. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  10. concentrationThe dried organic phase was concentrated
  11. concentrationA fraction of the intended title compound was concentrated
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-08a1b3ede823469a9260452692cd1161
Source dataset
uspto-grants-1994_03
Patent number
US05298518

Reaction notes

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