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Quinaldic Acid → N-(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide

HRID 1772636
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HRID 1772636 반응식
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:47][C:48]1[N:53]2[CH:54]=[C:55]([NH2:57])[N:56]=[C:52]2[C:51]([N:58]2[CH2:63][CH2:62][O:61][CH2:60][CH2:59]2)=[N:50][CH:49]=1>C(Cl)Cl>[Br:47][C:48]1[N:53]2[CH:54]=[C:55]([NH:57][C:1]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[O:13])[N:56]=[C:52]2[C:51]([N:58]2[CH2:59][CH2:60][O:61][CH2:62][CH2:63]2)=[N:50][CH:49]=1
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참가 물질

6

반응물 4

HCID 7124Quinaldic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1177280545-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-amine

생성물 1

HCID 117728149N-(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of quinaldic acid (236 mg, 1.36 mmol) in DCM (10 mL) were added HATU (519 mg, 1.36 mmol) and DIEA (201 μL, 1.15 mmol) at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and treated with compound 21b (313 mg, 1.04 mmol). The resulting mixture was stirred at rt overnight. The solids formed were collected by filtration, and the organic phase was washed with saturated aqueous NH4Cl (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (9:1 DCM/EtOAc) to give compound 21c. Mass Spectrum (LCMS, ESI pos.) Calcd. for C20H17BrN6O2: 453.0 (M+H). Found 453.1.

후처리

  1. stirringThe resulting mixture was stirred at rt overnight
  2. customThe solids formed
  3. filtrationwere collected by filtration
  4. washthe organic phase was washed with saturated aqueous NH4Cl (20 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography on silica gel (9:1 DCM/EtOAc)

출처 및 근거

ORD 기록
ord-10484760c5034bff830bcc821c9f9bec
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249163B2

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