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

HRID 1944917Notes

Reaction equation

HRID 1944917 reaction equation
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

Participants

8

Reactant 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

Product 1

HCID 669880454-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-(3-(2-oxopropyl)benzoyl)piperazine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamideYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-fdb2b8154e52486e950845ae21b1fd0f
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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