Diisopropylethylamine → HCID 86700030, compound

HRID 1428079Notes

Reaction equation

HRID 1428079 reaction equation
C1C=NC2N(O)N=NC=2C=1.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.[F:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[C:52](=[O:61])[C:53]([C:58]([OH:60])=O)=[CH:54][N:55]([CH3:57])[CH:56]=2)=[CH:47][CH:46]=1.[NH2:62][C:63]1[CH:68]=[CH:67][C:66]([C:69]2[C:70]([NH2:85])=[N:71][CH:72]=[C:73]([C:75]3[CH:80]=[CH:79][C:78]([O:81][CH3:82])=[C:77]([O:83][CH3:84])[CH:76]=3)[CH:74]=2)=[CH:65][CH:64]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:85][C:70]1[C:69]([C:66]2[CH:65]=[CH:64][C:63]([NH:62][C:58]([C:53]3[C:52](=[O:61])[C:51]([C:48]4[CH:47]=[CH:46][C:45]([F:44])=[CH:50][CH:49]=4)=[CH:56][N:55]([CH3:57])[CH:54]=3)=[O:60])=[CH:68][CH:67]=2)=[CH:74][C:73]([C:75]2[CH:80]=[CH:79][C:78]([O:81][CH3:82])=[C:77]([O:83][CH3:84])[CH:76]=2)=[CH:72][N:71]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 602042125-(4-Fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidHCID 86700031HCID 86700031, compound

Product 1

HCID 86700030HCID 86700030, compoundYield 20.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOAt (23 mg), HATU (97 mg), DMAP (10 mg) and DIPEA (50 μl) were added to a solution of 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid (46 mg) in DMF (1 ml) at room temperature. The reaction mixture was stirred at room temperature for three hours. The compound obtained in Step 2 of Example 1 (55 mg) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified by PLC [ethyl acetate:methanol=20:1 (v/v)] to give 19 mg of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe resulting solid was purified by PLC [ethyl acetate:methanol=20:1 (v/v)]

Sources & evidence

ORD record
ord-1becf47f132e4710b3dffbef92656926
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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