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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
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HRID 1177652 반응식
[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
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857
Ethyl Acetate
용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f4afee656d2c412ca666085feb4cf3c2
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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