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Diisopropylethylamine → 3-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-5-fluoro-4-methyl-benzoic acid, methyl ester

HRID 337085
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인쇄 미리보기

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HRID 337085 반응식
[CH3:1][C:2]([CH3:18])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:3].Br[C:20]1[C:21](=[O:39])[N:22]([C:27]2[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=2[CH3:37])[C:30]([O:32][CH3:33])=[O:31])[CH:23]=[C:24]([Br:26])[N:25]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[Br:26][C:24]1[N:25]=[C:20]([NH:3][C:2]([CH3:18])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:1])[C:21](=[O:39])[N:22]([C:27]2[CH:28]=[C:29]([CH:34]=[C:35]([F:38])[C:36]=2[CH3:37])[C:30]([O:32][CH3:33])=[O:31])[CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 666888502-(2-(Benzyloxy)phenyl)propan-2-amineHCID 66689945methyl 3-(3,5-dibromo-2-oxo-1(2H)-pyrazinyl)-5-fluoro-4-methylbenzoate

생성물 1

HCID 866632493-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-5-fluoro-4-methyl-benzoic acid, methyl ester수율 83.2%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A solution of α,α-dimethyl-2-(phenylmethoxy)-benzenemethanamine (Example 198d, 5.25 g) dissolved in dioxane (40 mL) was treated with 3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-5-fluoro-4-methyl-benzoic acid, methyl ester (Example 252g, 9.14 g) and N,N-diisopropylethylamine (5.59 mL) under nitrogen. The resulting solution was stirred at 100° C. for 10 h. The reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (100 mL×2). The organic was dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography eluting with 20% ethyl acetate in iso-hexane) to afford the subtitle product (10.50 g).

후처리

  1. extractionextracted with ethyl acetate (100 mL×2)
  2. dry with materialThe organic was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified
  6. wash(SiO2 chromatography eluting with 20% ethyl acetate in iso-hexane)

출처 및 근거

ORD 기록
ord-d200ed8e3cb84a4aa67947adae6ddcbb
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889692B2

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