Diisopropylethylamine → HCID 86705186, compound

HRID 2401282Notes

Reaction equation

HRID 2401282 reaction equation
C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:34][C:35]1[CH:36]=[C:37]([CH:39]=[C:40]([F:42])[CH:41]=1)[NH2:38].[CH3:43][O:44][C:45]1[N:50]=[CH:49][C:48]([N:51]2[CH2:55][CH:54]([CH2:56][CH2:57][CH3:58])[N:53]([CH2:59][C:60](O)=[O:61])[C:52]2=[O:63])=[CH:47][CH:46]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:34][C:35]1[CH:36]=[C:37]([NH:38][C:60](=[O:61])[CH2:59][N:53]2[CH:54]([CH2:56][CH2:57][CH3:58])[CH2:55][N:51]([C:48]3[CH:49]=[N:50][C:45]([O:44][CH3:43])=[CH:46][CH:47]=3)[C:52]2=[O:63])[CH:39]=[C:40]([F:42])[CH:41]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 965953,5-DifluoroanilineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86705187HCID 86705187, compound

Product 1

HCID 86705186HCID 86705186, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N,N-diisopropylethylamine (0.06 mL), HATU (142 mg), and 3,5-difluoroaniline (48 mg) were added to a solution of [3-(6-methoxypyridin-3-yl)-2-oxo-5-propylimidazolidin-1-yl]acetic acid (100 mg) in chloroform (2 mL), and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford the title compound (114 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5abc00f3e22546c1aa9a3dfb1ba12ee0
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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