Diisopropylethylamine → 4-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[3-(2-oxopropyl)phenylcarbonyl(methyl)amino]methyl]phenyl]sulfonyl]quinoline-3-carboxamide

HRID 1944948Notes

Reaction equation

HRID 1944948 reaction equation
[O:1]=[C:2]([CH3:13])[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[C:37]([CH3:54])[CH:38]=[C:39]([S:42]([C:45]4[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][NH:52][CH3:53])[CH:46]=4)(=[O:44])=[O:43])[CH:40]=3)[N:35]=[CH:34][C:33]=2[C:55]([NH2:57])=[O:56])[CH:28]=[CH:29][CH:30]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[C:37]([CH3:54])[CH:38]=[C:39]([S:42]([C:45]4[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]([C:7]([C:6]5[CH:10]=[CH:11][CH:12]=[C:4]([CH2:3][C:2](=[O:1])[CH3:13])[CH:5]=5)=[O:9])[CH3:53])[CH:46]=4)(=[O:43])=[O:44])[CH:40]=3)[N:35]=[CH:34][C:33]=2[C:55]([NH2:57])=[O:56])[CH:28]=[CH:29][CH:30]=1

Participants

7

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 669882324-[(3-Methoxyphenyl)amino)-8-methyl-6-[[3-[(methylamino)methyl]phenyl]sulfonyl]quinoline-3-carboxamide

Product 1

HCID 669882814-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[3-(2-oxopropyl)phenylcarbonyl(methyl)amino]methyl]phenyl]sulfonyl]quinoline-3-carboxamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-Oxopropyl)benzoic acid (33 mg, 0.185 mmol) and DIEA (0.097 mL, 0.555 mmol) were added to a stirring solution of Intermediate 136 (100 mg, 0.204 mmol) in DMF (2 mL) at rt. The reaction mixture was stirred for 5 min and HATU (78 mg, 0.204 mmol) was added. The resulting solution was stirred for 3 h then poured into H2O (50 mL). The precipitate was filtered, washed with H2O (30 mL), and dried to give the title compound (106 mg) as a yellow solid. ES/MS calcd for C36H35N4O6S+ 651.2. Found m/z=651.4 (M+H)+.

Workup

  1. stirringThe resulting solution was stirred for 3 h
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O (30 mL)
  4. customdried

Sources & evidence

ORD record
ord-66317ed829c241148fee32dea888c9dc
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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