Potassium Carbonate → HCID 71288191、化合物

HRID 245930ノート

反応式

HRID 245930 の反応式
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C@H:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:13]=1)=[O:11])[CH3:8])=O.CCN(S(F)(F)F)CC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:1]1[CH2:2][CH2:3][N:4]=[C:5]1[C@H:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[CH:13]=1)=[O:11])[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 712881872-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-amide

生成物 1

HCID 71288191HCID 71288191、化合物収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-76 °C

実験手順

In a round-bottomed flask, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-amide (126 mg, 0.23 mmol) was dissolved in dichloromethane (2.2 ml). The solution was cooled to −76° C. and DAST (45 μl, 0.34 mmol) was added. The pale yellow reaction mixture was stirred at −76° C. for 6 h then anhydrous potassium carbonate (64 mg, 0.46 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature, quenched with saturated aqueous NaHCO3 and extracted with dichloromethane (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-90% EtOAc) to afford 86 mg (71%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4,5-dihydro-oxazol-2-yl)-ethyl]-amide as a light yellow solid.

後処理

  1. temperatureto warm to room temperature
  2. customquenched with saturated aqueous NaHCO3
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-90% EtOAc)

出典と根拠

ORDレコード
ord-e0b71cac531f4477a2e5559cd5c85da0
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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