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Triethylamine → 3-{1-[5-(6-Bromopyridin-2-yl)-thiazol-2-yl]piperidin-4-yl}propionic acid methyl ester

HRID 1716522
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HRID 1716522 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Cl)[N:3]=1.[CH3:10][O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[S:23])[NH2:22])[CH2:17][CH2:16]1.[CH3:25]OC(OC)N(C)C.C(N(CC)CC)C>C(O)C>[CH3:10][O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[S:23][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[N:3]=3)=[CH:25][N:22]=2)[CH2:17][CH2:16]1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 216984342-Bromo-6-(chloromethyl)pyridineHCID 451186894-Piperidinepropanoic acid,1-(aminothioxomethyl)-,methyl ester

생성물 1

HCID 587064873-{1-[5-(6-Bromopyridin-2-yl)-thiazol-2-yl]piperidin-4-yl}propionic acid methyl ester수율 164.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To an solution of 2-bromo-6-chloromethylpyridine (1.88 g, 1.11 mmol) obtained in Step 1 of Example 1 in ethanol (20 ml), 3-(1-thiocarbamoylpiperidin-4-yl)propionic acid methyl ester (2.10 g, 9.12 mmol) obtained in Step 1 was added and the mixture was heated at reflux overnight. The reaction solution was cooled to room temperature, dimethylformamide dimethylacetal (1.8 ml, 14 mmol) and triethylamine (3.8 ml, 27 mmol) were added, and heated at reflux for 1 hour. After the reaction solution was concentrated, water was added, and it was extracted with ethyl acetate and washed with a saturated brine. The organic layer was dried over magnesium sulfate and the residue obtained by vacuum concentration was purified by chromatography on silica gel (n-hexane:ethyl acetate=50:50 to 0:100) and the title compound (748 mg, 20%) was obtained.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureheated
  4. temperatureat reflux for 1 hour
  5. concentrationAfter the reaction solution was concentrated
  6. additionwater was added
  7. extractionit was extracted with ethyl acetate
  8. washwashed with a saturated brine
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customthe residue obtained by vacuum concentration
  11. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=50:50 to 0:100)

출처 및 근거

ORD 기록
ord-47bc38572a3e4029962996a8e3a5ac1d
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803801B2

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