Diisopropylethylamine → HCID 66713971, compound

HRID 539655Notes

Reaction equation

HRID 539655 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1)([CH3:6])[C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:40][C:41]1[CH:58]=[CH:57][C:44]([CH2:45][C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:49](=[O:56])[NH:48][N:47]=2)=[CH:43][C:42]=1[C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)(Cl)Cl.C(OCC)(=O)C.CO>[F:40][C:41]1[CH:58]=[CH:57][C:44]([CH2:45][C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:49](=[O:56])[NH:48][N:47]=2)=[CH:43][C:42]=1[C:59]([N:61]1[CH2:66][CH2:65][N:64]([C:3](=[O:5])[C:2]([CH3:1])([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)[CH3:6])[CH2:63][CH2:62]1)=[O:60]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 117263994-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-oneHCID 160983422-Methyl-2-(5-(trifluoromethyl)pyridin-2-yloxy)propanoic acid

Product 1

HCID 66713971HCID 66713971, compoundYield 47.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanoic acid (0.204 g, 0.81 mmol) in dry DMF (6 mL) was added TBTU (0.289 g, 0.90 mmol) at room temperature under atmosphere of nitrogen. To this 4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one (0.3 g, 0.81 mmol) and DIPEA (0.303 mL, 1.74 mmol) were added. The reaction mixture was stirred at room temperature for 2 h. The progress of reaction was checked by TLC by using mobile phase 5% methanol in chloroform. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4 and solvents were evaporated on a rotatory evaporator under reduced pressure to crude solid which was purified by the flash column chromatography using eluent chloroform:methanol (98.3:1.7) to afford 4-(4-fluoro-3-(4-(2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanoyl)piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one as white solid (0.230 g, 47%).

Workup

  1. customThe progress of reaction
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4 and solvents
  4. customwere evaporated on a rotatory evaporator under reduced pressure to crude solid which
  5. customwas purified by the flash column chromatography

Sources & evidence

ORD record
ord-1611b0dc2e814def9926cac37a8d49f1
Source dataset
uspto-grants-2014_10
Patent number
US08871765B2

Reaction notes

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