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m-Chloroperbenzoic acid → 1-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-ol

HRID 1064253
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HRID 1064253 반응식
[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11](SC)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2].C([Si](C(C)C)(C(C)C)[N:24]1[C:28]2=[N:29][CH:30]=[C:31]([NH2:33])[CH:32]=[C:27]2[CH:26]=[CH:25]1)(C)C.ClC1C=CC=C(C(OO)=O)C=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)(Cl)Cl.C1COCC1>[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11]([NH:33][C:31]1[CH:32]=[C:27]3[CH:26]=[CH:25][NH:24][C:28]3=[N:29][CH:30]=1)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 70297m-Chloroperbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 222736141H-Pyrrolo[2,3-B]pyridin-5-amine, 1-[tris(1-methylethyl)silyl]-HCID 222736261-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol

생성물 1

HCID 222736641-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-ol
수율 1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

1-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol (262 mg, 0.93 mmol, obtained from Example 25 using procedure in Step B of Example 7) and 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (290 mg, 0.93 mmol) were dissolved in chloroform and m-chloroperbenzoic acid (60%, 535 mg, 1.86 mmol) was added. The mixture was heated at 120° C. for 10 min in a Personal Chemistry Smith Enrys Optimizer™ microwave oven. The solution was evaporated in vacuo and the residue was purified by preparative HPLC. The isolated product was dissolved in of THF (10 mL) and TBAF (1.0 M, 0.2 mL, 0.2 mmol) was added. The mixture was stirred for 5 min. and the solvent was evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound (3 mg, 1%).

후처리

  1. customThe solution was evaporated in vacuo
  2. customthe residue was purified by preparative HPLC
  3. additionwas added
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-0aec2b7d11964268bdd963de1046b90f
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06969717B2

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