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Diisopropylethylamine → 4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-(3-(2-oxopropyl)benzoyl)piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide

HRID 1944917
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HRID 1944917 반응식
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.[O:34]=[C:35]([CH3:46])[CH2:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40]([OH:42])=O.[CH3:47][O:48][C:49]1[CH:50]=[C:51]([NH:55][C:56]2[C:65]3[C:60](=[C:61]([CH3:83])[CH:62]=[C:63]([S:66]([C:69]4[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([N:77]5[CH2:82][CH2:81][NH:80][CH2:79][CH2:78]5)=[O:76])[CH:70]=4)(=[O:68])=[O:67])[CH:64]=3)[N:59]=[CH:58][C:57]=2[C:84]([NH2:86])=[O:85])[CH:52]=[CH:53][CH:54]=1>CN(C=O)C.C(Cl)Cl.CO.O>[CH3:47][O:48][C:49]1[CH:50]=[C:51]([NH:55][C:56]2[C:65]3[C:60](=[C:61]([CH3:83])[CH:62]=[C:63]([S:66]([C:69]4[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([N:77]5[CH2:78][CH2:79][N:80]([C:40](=[O:42])[C:39]6[CH:43]=[CH:44][CH:45]=[C:37]([CH2:36][C:35](=[O:34])[CH3:46])[CH:38]=6)[CH2:81][CH2:82]5)=[O:76])[CH:70]=4)(=[O:68])=[O:67])[CH:64]=3)[N:59]=[CH:58][C:57]=2[C:84]([NH2:86])=[O:85])[CH:52]=[CH:53][CH:54]=1
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참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 122541053-(2-Oxopropyl)benzoic acidHCID 669883114-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide

생성물 1

HCID 66988045
4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-(3-(2-oxopropyl)benzoyl)piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide
수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 21226129Dichloromethane methanol용매

실험 절차

HATU (82 mg, 0.217 mmol), DIEA (0.103 mL, 0.59 mmol), and 3-(2-oxopropyl)benzoic acid (39 mg, 0.217 mmol) were added to a stirring solution of Intermediate 96 (110 mg, 0.197 mmol) in DMF (2 mL) at rt. The reaction mixture was stirred for 40 min then pour into H2O (50 mL). The resulting precipitate was filtered, washed with H2O, and dried to give crude di-amide (256 mg). Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (85 mg, 64%) as a yellow solid. ES/MS calcd. for C39H38N5O7S+ 720.3. Found m/z=720.2 (M+H)+.

후처리

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O
  3. customdried
  4. customto give crude di-amide (256 mg)

출처 및 근거

ORD 기록
ord-fdb2b8154e52486e950845ae21b1fd0f
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394829B2

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