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Trifluoroacetic acid → HCID 54588864, 화합물

HRID 1396171
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HRID 1396171 반응식
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH:10][C:11]3[N:16]=[C:15]([F:17])[C:14]([CH:18]([C:20]4[C:28]5[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=5[N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=4)O)=[CH:13][CH:12]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([CH2:18][C:20]4[C:28]5[C:27]([O:29][CH3:30])=[N:26][CH:25]=[N:24][C:23]=5[NH:22][CH:21]=4)=[C:15]([F:17])[N:16]=3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 67445534[6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

생성물 1

HCID 54588864HCID 54588864, 화합물수율 25.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
80 °C

실험 절차

To [6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (73, 70 mg, 0.12 mmol) in 10.0 mL of 1,2-dichloroethane, triethylsilane (1.00 mL, 6.26 mmol) and trifluoroacetic acid (0.60 mL, 7.8 mmol) are added and the reaction stirred at 80° C. for 4 hours. The reaction is poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-4004, 11.8 mg). MS (ESI) [M+H+]+=390.9.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-8796848b84d1467092b4cfe31169c29d
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901118B2

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