Potassium Iodide → 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric acid ethyl ester

HRID 11718

반응식

HRID 11718 반응식
[NH2:1][C:2]1[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][C@H:17]([CH3:19])[N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:15][C@H:14]2[CH3:28])=[O:12])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35]Br)[CH3:30].C(=O)(O)[O-].[Na+].[I-].[K+].C(OC(=O)C(Br)CC)C>C(O)C>[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35][NH:1][C:2]1[C:3]([O:9][CH2:10][C:11]([N:13]2[CH2:18][C@H:17]([CH3:19])[N:16]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH2:15][C@H:14]2[CH3:28])=[O:12])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH3:30]

참가 물질

7

반응물 5

HCID 4875Potassium IodideHCID 76300Ethyl 4-bromobutyrateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 516892Sodium BicarbonateHCID 696555902-(3-Amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

생성물 1

HCID 696559714-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-butyric acid ethyl ester수율 36.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2-(3-amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.072 g, 0.18 mmol) in ethanol (1 mL) was added 4-bromo-butyric acid ethyl ester (0.030 mL, 0.21 mmol), sodium bicarbonate (0.031 g, 0.37 mmol) and potassium iodide (˜0.030 g). The resulting solution was stirred at 70° C. for 18 hours. Additional bromo-butyric acid ethyl ester (0.030 mL, 0.21 mmol) was added and the reaction was stirred at 70° C. for 18 hours. The reaction was cooled, concentrated in vacuo and purified via flash chromatography on silica gel to give the title compound (0.034 g).

후처리

  1. stirringthe reaction was stirred at 70° C. for 18 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. custompurified via flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-5c62ce052f7a4c5586df582a6416f915
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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