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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-(Isoindolin-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

HRID 1177652
ノート
印刷プレビュー

反応式

HRID 1177652 の反応式
[C:1]1([C:7]2([C:10]3[NH:15][C:14](=[S:16])[C:13]([NH:17][C:18]([C:20]4[CH:21]=[C:22]5[C:26](=[CH:27][CH:28]=4)[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]5)=O)=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:25]1[C:26]2[C:22](=[CH:21][C:20]([C:18]3[S:16][C:14]4[C:13]([N:17]=3)=[CH:12][CH:11]=[C:10]([C:7]3([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH2:8][CH2:9]3)[N:15]=4)=[CH:28][CH:27]=2)[CH2:23][NH:24]1
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

5

反応物 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 86638729Tert-butyl 5-(6-(1-phenylcyclopropyl)-2-thioxo-1,2-dihydropyridin-3-ylcarbamoyl)isoindoline-2-carboxylate

生成物 1

HCID 671117342-(Isoindolin-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
100 °C

実験手順

tert-Butyl 5-(6-(1-phenylcyclopropyl)-2-thioxo-1,2-dihydropyridin-3-ylcarbamoyl)i-soindoline-2-carboxylate (213 mg, 0.437 mmol) was dissolved in toluene (4.4 mL) before camphor sulfonic acid (91 mg, 0.393 mmol) was added and stirred at 100° C. for 3 h. The reaction mixture was diluted with 75 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give 2-(isoindolin-5-yl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine after flash chromatography. MS (ESI) m/z: Calculated: 369.1; Observed: 370.4 (M++H).

後処理

  1. additionwas added
  2. additionadded to a separatory funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed with sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap

出典と根拠

ORDレコード
ord-f4afee656d2c412ca666085feb4cf3c2
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842685B2

反応ノート

読み込み中…

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