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N-methyl-2-pyrrolidone → tert-butyl {(2S)-1-[(5-bromo-6-cyanopyridin-3-yl)amino]propan-2-yl}carbamate

HRID 1504857
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인쇄 미리보기

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HRID 1504857 반응식
[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](F)[CH:7]=1.Cl.[NH2:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].CCN(C(C)C)C(C)C.CN1CCCC1=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([NH:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]
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참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 469414773-Bromo-5-fluoropicolinonitrileHCID 53350397(S)-tert-Butyl (1-aminopropan-2-yl)carbamate hydrochloride

생성물 1

HCID 86731723tert-butyl {(2S)-1-[(5-bromo-6-cyanopyridin-3-yl)amino]propan-2-yl}carbamate

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

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온도
150 °C

실험 절차

To a microwave vial were added 3-bromo-5-fluoropyridine-2-carbonitrile (150 mg, 0.746 mmol), tert-butyl [(2S)-1-aminopropan-2-yl]carbamate hydrochloride (157 mg, 0.755 mmol), DIPEA (0.260 mL, 1.49 mmol), and N-methyl-2-pyrrolidone (1.5 mL). The mixture was then heated by microwave irradiation to a temperature of 150° C. for 30 minutes. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate and washed with water. The organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford tert-butyl {(2S)-1-[(5-bromo-6-cyanopyridin-3-yl)amino]propan-2-yl}carbamate. MS ESI calc'd. for C14H20BrN4O2 [M+H]+ 355 and 357. found 355 and 357.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-9ef219f3b41147879b1b67cc1df789af
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216173B2

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