Iodoethane → Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

HRID 626619노트

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HRID 626619 반응식
[NH2:1][C:2]1[C:7](NC(=O)OC)=[C:6]([NH2:13])[N:5]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:3]=1.C[Si]([N-:36][Si](C)(C)C)(C)C.[Na+].I[CH2:43][CH3:44].[C:45]([O:48][CH2:49]C)(=[O:47])C>C1COCC1>[NH2:13][C:6]1[C:7]([CH2:44][CH2:43][NH:36][C:45](=[O:47])[O:48][CH3:49])=[C:2]([NH2:1])[N:3]=[C:4]([N:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[C:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:15]2)[N:5]=1

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 56963347Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate

생성물 1

HCID 86698876Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}ethylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Under argon, 142 mg (0.33 mmol) of the compound from example 1 were initially charged in THF (9.5 ml), the mixture was cooled to 0° C. and 0.33 ml (0.33 mmol) of sodium bis(trimethylsilyl)amide (1.0 M in THF) was then added dropwise. The mixture was stirred at 0° C. for 30 min, and 35 μl (0.43 mmol) of iodoethane were then added dropwise. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1) and the product fractions were concentrated. This gave 89 mg (59% of theory) of the title compound as a solid.

후처리

  1. stirringThe reaction mixture was stirred at RT overnight
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (mobile phase dichloromethane:methanol 60:1)
  7. concentrationthe product fractions were concentrated

출처 및 근거

ORD 기록
ord-ee831e6ded404dda843f810e2978b050
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309239B2

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