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Hydrogen Peroxide → (R)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)-2-hydroxyethylamino)nicotinamide

HRID 75864
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인쇄 미리보기

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HRID 75864 반응식
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([F:18])=[CH:16][C:13]([C:14]#[N:15])=[C:12]([NH:19][C@H:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:21][OH:22])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-:30].[K+].OO>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([F:18])=[CH:16][C:13]([C:14]([NH2:15])=[O:30])=[C:12]([NH:19][C@H:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:21][OH:22])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 11574786(R)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)-2-hydroxyethylamino)nicotinonitrile

생성물 1

HCID 67456878(R)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)-2-hydroxyethylamino)nicotinamide수율 90%

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
65 °C

실험 절차

(R)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)-2-hydroxyethylamino)nicotinonitrile (Example 6; 0.07 g, 0.2 mmol), was placed in MeOH (5 ml) at 25° C. A 25% aqueous solution (0.2 ml) of KOH (50 mg) was then added, followed by the addition of 0.05 ml of 30% H2O2. The resulting dark red solution was heated to 65° C. for 1 h, cooled to 25° C., and concentrated. The resulting residue was dissolved in EtOAc (50 ml), washed with water (30 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM-MeOH=30:1) to give the title compound (0.065 g, 90%). 1H NMR (400 MHz, CD3OD) δ 7.69 (d, J=12.1 Hz, 1H), 7.39-7.36 (m, 2H), 7.04-7.00 (m, 2H), 5.94 (s, 1H), 5.22-5.16 (m, 1H), 3.87-3.75 (m, 2H), 1.91-1.84 (m, 1H), 0.98-0.96 (m, 2H), 0.74-0.69 (m, 2H). MS: Calcd.: 414. Found: [M+H]+ 415.

후처리

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in EtOAc (50 ml)
  4. washwashed with water (30 ml)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was purified by column chromatography (DCM-MeOH=30:1)

출처 및 근거

ORD 기록
ord-ecbddbc67ee749d7a5a6992a3b603551
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835465B2

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