Diisopropylethylamine → 2-fluoro-N-methyl-4-[3-(quinolin-6-ylthio)imidazo[1,2-a]pyrimidin-6-yl]benzamide

HRID 1257790노트

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HRID 1257790 반응식
C(N(CC)C(C)C)(C)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:53]1[N:57]2[CH:58]=[C:59]([C:62]3[CH:71]=[CH:70][C:65]([C:66]([NH:68][CH3:69])=[O:67])=[C:64]([F:72])[CH:63]=3)[CH:60]=[N:61][C:56]2=[N:55][CH:54]=1.[N:73]1[C:82]2[C:77](=[CH:78][C:79]([SH:83])=[CH:80][CH:81]=2)[CH:76]=[CH:75][CH:74]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:72][C:64]1[CH:63]=[C:62]([C:59]2[CH:60]=[N:61][C:56]3[N:57]([C:53]([S:83][C:79]4[CH:78]=[C:77]5[C:82](=[CH:81][CH:80]=4)[N:73]=[CH:74][CH:75]=[CH:76]5)=[CH:54][N:55]=3)[CH:58]=2)[CH:71]=[CH:70][C:65]=1[C:66]([NH:68][CH3:69])=[O:67]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23422228Quinoline-6-thiolHCID 672244434-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide

생성물 1

HCID 251456602-fluoro-N-methyl-4-[3-(quinolin-6-ylthio)imidazo[1,2-a]pyrimidin-6-yl]benzamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

N,N-Diisopropylethylamine (70 μL, 0.4 mmol), tris(dibenzylideneacetone)-dipalladium(0) (4.58 mg, 0.0050 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.79 mg, 0.010 mmol) was added successively to a solution of 4-(3-bromoimidazo[1,2-a]pyrimidin-6-yl)-2-fluoro-N-methylbenzamide (69.8 mg, 0.2 mmol) and quinoline-6-thiol (32.2 mg, 0.2 mmol) in 1,4-dioxane (0.42 mL) in a microwave tube. The tube was sealed and degassed three times, and heated to 100° C. overnight. After cooling, the reaction mixture was diluted with methanol, and filtered. The filtrate was purified by RP-HPLC (pH 10) to give the desired product. LCMS: (M+H)=430.0.

후처리

  1. customThe tube was sealed
  2. customdegassed three times
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with methanol
  5. filtrationfiltered
  6. customThe filtrate was purified by RP-HPLC (pH 10)

출처 및 근거

ORD 기록
ord-422121383c9a4fb987bed3ab48c785ea
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461330B2

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