Carbon Dioxide → 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 1052270ノート

反応式

HRID 1052270 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([CH2:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)[N:9]=2)[N:4]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:3]=1[C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1.C([Li])CCC.[C:49](=[O:51])=[O:50]>O1CCCC1>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:8]2[N:9]=[C:10]3[C:2]([C:49]([OH:51])=[O:50])=[C:3]([C:31]4[CH:36]=[CH:35][C:34]([N:37]5[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]5)=[CH:33][CH:32]=4)[N:4]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:5]3=[N:6][CH:7]=2)[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1

参加物

5

反応物 3

HCID 280Carbon Dioxide2 回HCID 899624757-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]-pyrazineHCID 178418339Butyllithium

生成物 1

HCID 899630612-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The a stirred solution of 7-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]-pyrazine (55 mg, 82.7 μmol) in tetrahydrofuran (2 mL), n-butyllithium (2.5 M in hexanes, 50 μL, 0.125 mmol) was added at 78° C. After 10 minutes, dry CO2 (prepared by passing the CO2 through drying tube) was bubbled into the reaction. After 20 minutes, the reaction was quenched with saturated aqueous NH4Cl, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, then concentrated to give the crude product (50 mg), which was used directly in the next step. LCMS calculated for C34H46BN5O5Si (M+H)+: m/z=632.3. Found: 632.3.

後処理

  1. customthrough drying tube)
  2. customwas bubbled into the reaction
  3. waitAfter 20 minutes
  4. customthe reaction was quenched with saturated aqueous NH4Cl
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c6f1b42825ae4396badc0e5a8aa4aaf8
出典データセット
uspto-grants-2016_07
特許番号
US09388185B2

反応ノート

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