Diethyl Ether → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-3-methyl-cyclopentyl)-N-pyrazin-2-yl-propionamide

HRID 854831노트

반응식

HRID 854831 반응식
C[Mg]Br.CC[O:6][CH2:7][CH3:8].[Cl:9][C:10]1[CH:11]=[C:12]([CH:20]([CH2:30][CH:31]2[CH2:35]C[C:33](=O)[CH2:32]2)[C:21]([NH:23][C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)=[O:22])[CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17]>O1CCCC1>[Cl:9][C:10]1[CH:11]=[C:12]([CH:20]([CH2:30][CH:31]2[CH2:32][CH2:33][C:7]([OH:6])([CH3:8])[CH2:35]2)[C:21]([NH:23][C:24]2[CH:29]=[N:28][CH:27]=[CH:26][N:25]=2)=[O:22])[CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:17])=[O:18]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 10477292Piragliatin;RO 4389620HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 100717912-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-3-methyl-cyclopentyl)-N-pyrazin-2-yl-propionamide수율 35.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

3.0M solution of methylmagnesium bromide in ether (2.53 mL, 7.59 mmol) cooled to 0° C. was treated dropwise with a solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide (prepared as in Example 45, 0.10 g, 0.237 mmol) in tetrahydrofuran (1 mL). The resulting solution was stirred at 0° C. for 30 min, quenched with a saturated aqueous ammonium chloride solution (3 mL), and partitioned between a saturated aqueous ammonium chloride solution (20 mL) and ethyl acetate (25 mL). The aqueous layer was extracted with ethyl acetate (25 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 80% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-hydroxy-3-methyl-cyclopentyl)-N-pyrazin-2-yl-propionamide (37 mg, 35%) as a yellow foam: mp 78-84° C. (foam to gel); (ES)+-HRMS m/e calcd for C20H24ClN3O4S (M+H)+ 438.1249. found 438.1254.

후처리

  1. customquenched with a saturated aqueous ammonium chloride solution (3 mL)
  2. custompartitioned between a saturated aqueous ammonium chloride solution (20 mL) and ethyl acetate (25 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (25 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bb0526429be7413b920cfc0e83c4f407
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259166B2

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