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Trifluoroacetic acid → 2-(2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl)-2-methyl propanenitrile

HRID 44671
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HRID 44671 반응식
[CH3:1][C:2]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[N:17](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:18]=[CH:19][C:12]=23)[S:9][CH:10]=1)([CH3:5])[C:3]#[N:4].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:17]1[C:13]2=[N:14][CH:15]=[CH:16][C:11]([C:8]3[S:9][CH:10]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[N:7]=3)=[C:12]2[CH:19]=[N:18]1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 666435592-Methyl-2-[2-(1-tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]propanenitrile

생성물 1

HCID 666456192-(2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl)-2-methyl propanenitrile수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-methyl-2-[2-(1-tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]propanenitrile (239 mg, 0.4671 mmol) in DCM (6 mL) was treated with triethylsilane (727.8 mg, 999.7 μL, 6.259 mmol) followed by dropwise addition of TFA (296.0 mg, 200.0 μL, 2.596 mmol). The mixture was allowed to stir for 1 hour and then concentrated in vacuo and purified by column chromatography (EtOAc) to give the desired product as a yellow solid (97.5 mg, 78% Yield). 1H NMR (DMSO, 400 MHz) δ 1.84 (6H, s), 7.73 (1H, d), 8.04 (1H, s), 8.64 (1H, s), 8.67 (1H, d), 13.98 (1H, br s); MS (ES+) 270.03

후처리

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (EtOAc)

출처 및 근거

ORD 기록
ord-ff23ababa25144aa9e6b441e09a4f2e8
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541445B2

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