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 1645523노트

반응식

HRID 1645523 반응식
[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]

참가 물질

6

반응물 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, 화합물

생성물 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-benzimidazole수율 52.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-97673d403b214a4c9117b3b81758b2f0
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124780B2

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