Triethylamine → HCID 54674793, compound

HRID 2251805Notes

Reaction equation

HRID 2251805 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH:5]1[CH3:17])[CH:2]=[CH2:3].[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([Cl:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])[CH3:19].C(N(CC)CC)C>O1CCCC1>[ClH:30].[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([NH:16][S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH:18]([CH3:20])[CH3:19])=[CH:22][CH:23]=3)(=[O:29])=[O:28])=[CH:12][CH:11]=2)[CH2:6][CH:5]1[CH3:17])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 69145987HCID 69145987, compound

Product 1

HCID 54674793HCID 54674793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

305 mg (1.31 mmol) of 6-(4-allyl-3-methylpiperazin-1-yl)pyridin-3-ylamine from Example 13.3 and 301 mg (1.38 mmol) of 4-isopropylbenzenesulfonyl chloride were dissolved in 10 ml of tetrahydrofuran at room temperature, after which 0.55 ml (3.94 mmol) of triethylamine was added dropwise. After that, the reaction mixture was stirred overnight at room temperature. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and the mixture was made acid with 1N hydrochloric acid and extracted twice with diethylether. The aqueous phase was made alkaline, to pH 9-10, using a 1N aqueous solution of sodium hydroxide and then extracted twice with diethyl ether. After the combined organic phases had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was purified by column chromatography (cyclohexane/ethylacetate from 50:50 to 20:80). After that, the filtrate was evaporated down to dryness. The resulting residue was converted into the hydrochloride using ethereal hydrochloric acid, with 417 mg (74% of theory) of the title compound being obtained.

Workup

  1. customAfter the solvent had been evaporated down to dryness
  2. additionthe resulting residue was treated with water
  3. extractionextracted twice with diethylether
  4. extractionextracted twice with diethyl ether
  5. dry with materialAfter the combined organic phases had been dried over sodium sulfate
  6. filtrationthe solvent had been filtered
  7. customevaporated down to dryness
  8. customthe resulting residue was purified by column chromatography (cyclohexane/ethylacetate from 50:50 to 20:80)
  9. customAfter that, the filtrate was evaporated down to dryness
  10. custombeing obtained

Sources & evidence

ORD record
ord-cf38b25f7beb4848b410e9cd78101a3a
Source dataset
uspto-grants-2008_01
Patent number
US07320979B2

Reaction notes

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