Triethylamine → HCID 44212503, compound

HRID 355740Notes

Reaction equation

HRID 355740 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.S(Cl)(Cl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:14][CH:13]=2)=[CH:23][C:22]=1[N:28]1[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 7365314-(1H-1,2,4-Triazol-1-yl)benzoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 44212503HCID 44212503, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-(1,2,4-triazol-1-yl)benzoate (520 mg, 2.4 mmol) was heated at reflux in 5N HCl (40 ml) for 1 h, and the product filtered off and dried in vacuo to afford the acid (88%). 4-(1,2,4triazol-1-yl)benzoic acid (0.395 g, 2.1 mmol) was suspended in dry toluene (40 ml) and thionyl chloride (2 ml) added under argon. The mixture was heated to reflux for 1.5 h and then evaporated to dryness under reduced pressure. The oil was dissolved in dichloromethane under argon and 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (460 mg, 2.1 mmol) was added followed by triethylamine (2 ml). The mixture was stirred at room temperature under argon for 2 h and then partitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml), and the organic extracts dried (sodium sulphate). The organic solution was filtered, evaporated to dryness under reduced pressure and purified by column chromatography (silica, chloroform/methanol 5-10%) to afford the amide (757 mg, 92%) which was crystallised from methanol diethyl ether as the oxalate salt.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. customevaporated to dryness under reduced pressure
  4. dissolutionThe oil was dissolved in dichloromethane under argon
  5. custompartitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml)
  6. dry with materialthe organic extracts dried (sodium sulphate)
  7. filtrationThe organic solution was filtered
  8. customevaporated to dryness under reduced pressure
  9. custompurified by column chromatography (silica, chloroform/methanol 5-10%)

Sources & evidence

ORD record
ord-1e01bc38112a42efaaea04ddc23ffefe
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

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