Triethylamine → HCID 69147108, compound

HRID 2251809Notes

Reaction equation

HRID 2251809 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(N(CC)CC)C>O1CCCC1>[ClH:29].[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=3)(=[O:28])=[O:27])=[N:14][CH:15]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 69145023HCID 69145023, compound

Product 1

HCID 69147108HCID 69147108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

520 mg (2.38 mmol) of 5-(4-allylpiperazin-1-yl)pyridin-2-ylamine and 495 mg (2.26 mmol) of 4-isopropylbenzenesulfonyl chloride were dissolved in 5 ml of tetrahydrofuran at room temperature, after which 1.0 ml (7.15 mmol) of triethylamine was added dropwise and the mixture was stirred at 40-50° C. for 6 hours. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and this mixture was made acid using 1N aqueous hydrochloric acid and extracted twice with diethyl ether. The aqueous phase was made alkaline, to pH 9-10, using a 1N aqueous solution of sodium hydroxide and then extracted twice with ethyl acetate. After the combined organic phases had been dried over sodium sulfate, the drying agent had been filtered off and the solvent had been evaporated down to dryness, the resulting residue was chromatographed on silica gel using ethyl acetate. After the solvent had been removed, the resulting residue was brought into solution using a little diethyl ether in dichloromethane and then converted into the hydrochloride using ethereal hydrochloric acid. 415 mg (44% of theory) of the title compound were obtained.

Workup

  1. customAfter the solvent had been evaporated down to dryness
  2. additionthe resulting residue was treated with water
  3. extractionextracted twice with diethyl ether
  4. extractionextracted twice with ethyl acetate
  5. dry with materialAfter the combined organic phases had been dried over sodium sulfate
  6. filtrationthe drying agent had been filtered off
  7. customthe solvent had been evaporated down to dryness
  8. customthe resulting residue was chromatographed on silica gel
  9. customAfter the solvent had been removed

Sources & evidence

ORD record
ord-56bbf5418d0d440eaadc8d2745c543c7
Source dataset
uspto-grants-2008_01
Patent number
US07320979B2

Reaction notes

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