Triethylamine → 2-(((4-(2-(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole

HRID 1645523ノート

反応式

HRID 1645523 の反応式
[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH2:22]O)[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][O:4]1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[SH:37][C:38]1[NH:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1>C1COCC1>[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH2:22][S:37][C:38]3[NH:42][C:41]4[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=4[N:39]=3)[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][O:4]1)[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59792375(4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanolHCID 178527775HCID 178527775、化合物

生成物 1

HCID 597925652-(((4-(2-(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole収率 52.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a THF (10 ml) solution of the (4-(2-(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanol (560 mg, 1.65 mmol) obtained in the step (4g), triethylamine (0.48 ml, 3.44 mmol) was added at room temperature and thereafter, methanesulfonyl chloride (0.19 ml, 2.45 mmol) was added while cooling in an ice salt bath and stirred under the same conditions for 30 minutes. After the ice salt bath was removed, 2-mercaptobenzimidazole (248 mg, 1.65 mmol) was added and stirred at room temperature for 22 hours. After the reaction mixture was concentrated, NH silica gel was added to the residue and dried. The crude substance was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0, 1/1-0/1 gradient) and a desired fraction(s) was concentrated. The obtained foamy product was dissolved in chloroform and diethyl ether was added thereto. The resulting solid was collected by filtration to obtain the title compound (410 mg, yield: 52.7%) as a white solid.

後処理

  1. additionwas added at room temperature
  2. temperaturewhile cooling in an ice salt bath
  3. customAfter the ice salt bath was removed
  4. stirringstirred at room temperature for 22 hours
  5. concentrationAfter the reaction mixture was concentrated
  6. additionNH silica gel was added to the residue
  7. customdried
  8. customThe crude substance was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0, 1/1-0/1 gradient)
  9. concentrationa desired fraction(s) was concentrated
  10. dissolutionThe obtained foamy product was dissolved in chloroform
  11. additiondiethyl ether was added
  12. filtrationThe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-97673d403b214a4c9117b3b81758b2f0
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

反応ノート

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