Diisopropylethylamine → 4-(1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide

HRID 2061822Notes

Reaction equation

HRID 2061822 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([NH:30][C:31]([NH:33][CH2:34][CH2:35][CH3:36])=[O:32])=[CH:19][C:20]=3[C:21]3[S:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:12][CH:13]=2)[C:8](=[O:37])[C:7]([C:38]([OH:40])=O)=[CH:6]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:75][N:76]([CH3:86])[S:77]([N:80]1[CH2:85][CH2:84][NH:83][CH2:82][CH2:81]1)(=[O:79])=[O:78]>CN(C)C=O>[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[N:17][C:18]([NH:30][C:31]([NH:33][CH2:34][CH2:35][CH3:36])=[O:32])=[CH:19][C:20]=3[C:21]3[S:22][CH:23]=[C:24]([C:26]([F:28])([F:27])[F:29])[N:25]=3)=[CH:12][CH:13]=2)[C:8](=[O:37])[C:7]([C:38]([N:83]2[CH2:82][CH2:81][N:80]([S:77]([N:76]([CH3:86])[CH3:75])(=[O:79])=[O:78])[CH2:85][CH2:84]2)=[O:40])=[CH:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1094966N,N-dimethylpiperazine-1-sulfonamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594157331-(2-(Dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 594159014-(1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid (Example 153, 80 mg, 0.14 mmol) in dimethylformamide (0.5 mL) was added HATU (78.4 mg, 0.20 mmol) then diisopropylethylamine (95.2 uL, 0.55 mmol). This was followed by N,N-dimethylpiperazine-1-sulfonamide (52.7 mg, 0.27 mmol) and the reaction was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and the residue purified by prep HPLC (Water-methanol-0.1% Formic acid).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by prep HPLC (Water-methanol-0.1% Formic acid)

Sources & evidence

ORD record
ord-37a31dc382854346bc665fbed688e510
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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