Triethylamine → HCID 54674793、化合物

HRID 444964ノート

反応式

HRID 444964 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 69145987HCID 69145987、化合物

生成物 1

HCID 54674793HCID 54674793、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5841ebd0578241aabb03c832aa6615df
出典データセット
uspto-grants-2013_07
特許番号
US08476275B2

反応ノート

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