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Acetic Acid → methyl (2S)-3-[4-(3-{[4-(1-fluoroethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate

HRID 595151
ノート
印刷プレビュー

反応式

HRID 595151 の反応式
Cl[C:2]1[N:7]=[C:6]([CH:8]([F:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.C(O)(=O)C.[NH2:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:24]=[N:25][N:26]([CH2:28][C@H:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31])[CH:27]=2)[CH:19]=[C:20]([CH3:22])[CH:21]=1>O1CCOCC1.O>[F:10][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:15][C:16]2[CH:17]=[C:18]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][C@H:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31])[CH:27]=3)[CH:19]=[C:20]([CH3:22])[CH:21]=2)[N:7]=1)[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 866582372-Chloro-4-(1-fluoroethyl)pyrimidineHCID 118216456methyl (2S)-3-[4-(3-amino-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate

生成物 1

HCID 118216465methyl (2S)-3-[4-(3-{[4-(1-fluoroethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
120 °C

実験手順

2-Chloro-4-(1-fluoroethyl)pyrimidine (58 mg, 0.36 mmol) and acetic acid (0.022 mL, 0.38 mmol) were added to an oven-dried flask containing methyl (2S)-3-[4-(3-amino-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate (100 mg, 0.36 mmol) in dioxane (1.2 mL). The mixture was stirred for 3 hours at 120° C. then cooled to room temperature, diluted with water, and extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (2 to 100% EtOAc/hexanes) to afford methyl (2S)-3-[4-(3-{[4-(1-fluoroethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]-2-hydroxypropanoate. MS ESI calcd. for C20H23FN5O3 [M+H]+ 400. found 400.

後処理

  1. temperaturethen cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (2 to 100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a5906c11644c452f8e73e3b26b4ab783
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242984B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート