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Ethyl Acetate → [3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester

HRID 849017
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인쇄 미리보기

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HRID 849017 반응식
Br[C:2]1[C:3](=[O:15])[N:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([CH3:8])=[CH:6][N:7]=1.[F:16][C:17]([F:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][NH2:19].C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:16][C:17]([F:26])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:18][NH:19][C:2]1[C:3](=[O:15])[N:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([CH3:8])=[CH:6][N:7]=1
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 1514288Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetateHCID 126355292,2-Difluoro-2-phenylethylamine

생성물 1

HCID 22179412[3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

To a stirred suspension of 507 mg (1.843mmol) of 7-4 in 10 ml of toluene was added 578 mg (3.68 mmol) of 7-6 via pipet. The reaction mixture was heated to 110° C. overnight. The solution was allowed to cool to room temperature and ethyl acetate was added. The diluted reaction mixture was washed with 10% hydrochloric acid. Three ethyl acetate extractions were performed on the aqueous layer. The organic layers were combined, dried (sodium sulfate), and concentrated in vacuo to give 745 mg of an off white solid. The solid was purified using a 40 mm column, 6 inches of silica gel and a 1:1 ethyl acetate/hexane solvent system to give 7-7 as a colorless solid: H1NMR CDCl3): δ 1.25 (t, 3H, 6.2 Hz), 2.1 (s, 3H), 4.0-4.1 (m, 2H), 4.25 (q, 2H, 7.1 Hz), 4.72 (s, 2H), 6.15 (s 1H), 6.68 (s, 1H) 7.4-7.6 (m, 3H), 7.6-7.8 (m, 2H).

후처리

  1. temperatureto cool to room temperature
  2. customThe diluted reaction mixture
  3. washwas washed with 10% hydrochloric acid
  4. extractionThree ethyl acetate extractions
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give 745 mg of an off white solid
  8. customThe solid was purified

출처 및 근거

ORD 기록
ord-082e302ab0a44bb3993bd9ec935dbb73
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06011038

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