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Methyl iodide → 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-methoxy-1-methyl-ethyl)-amide

HRID 246149
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HRID 246149 반응식
[OH:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[N:10]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:9]=1)=[O:7])[CH3:4].[CH3:36]I>[Ag]=O.CC#N>[CH3:36][O:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[N:10]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[CH:9]=1)=[O:7])[CH3:4]
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참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 712860912-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide

생성물 1

HCID 712860582-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-methoxy-1-methyl-ethyl)-amide수율 45%

시약·촉매·용매 2

HCID 92152
Silver(II) oxide
촉매
HCID 6342Acetonitrile용매

반응 조건

온도
40 °C

실험 절차

In a 25 mL round-bottomed flask, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide (70 mg, 0.136 mmol), silver oxide (51 mg, 0.22 mmol) and methyl iodide (100 μl, 1.6 mmol) were combined with MeCN to give a black suspension. The round bottom flask was wrapped in foil to exclude light. The system was placed in a sand bath and heated to 40° C. with stirring. The temperature was maintained for 2 days. Upon cooling, the reaction mixture was filtered through a pad a celite. The filtrate was concentrated. The crude material was purified by chromatography over SiO2 with EtOAc/hexanes (gradient: 0%-40% EtOAc) to afford 32 mg (45%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-methoxy-1-methyl-ethyl)-amide as an off-white solid. [M+Na]+=551.

후처리

  1. customto give a black suspension
  2. customThe system was placed in a sand bath
  3. temperatureThe temperature was maintained for 2 days
  4. temperatureUpon cooling
  5. filtrationthe reaction mixture was filtered through a pad a celite
  6. concentrationThe filtrate was concentrated
  7. customThe crude material was purified by chromatography over SiO2 with EtOAc/hexanes (gradient: 0%-40% EtOAc)

출처 및 근거

ORD 기록
ord-ab18c104e9b042248b7c68275cafc4d2
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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