Diisopropylethylamine → 2,6-Dichloro-N-[2-(4-morpholinyl)ethyl]-4-pyridinecarboxamide

HRID 2233837Notes

Reaction equation

HRID 2233837 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([Cl:54])[N:53]=1)[C:48]([OH:50])=O.[N:55]1([CH2:61][CH2:62][NH2:63])[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>CC(N(C)C)=O>[Cl:54][C:52]1[CH:51]=[C:47]([CH:46]=[C:45]([Cl:44])[N:53]=1)[C:48]([NH:63][CH2:62][CH2:61][N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)=[O:50]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 948302,6-Dichloroisonicotinic acidHCID 181649HOAtHCID 4082852-MorpholinoethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 432358692,6-Dichloro-N-[2-(4-morpholinyl)ethyl]-4-pyridinecarboxamideYield 105%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

HATU (989 mg, 2.6 mmol), HOAT (354 mg, 2.6 mmol) and DIEA (907 μl, 5.21 mmol) were added to a stirred solution of 2,6-dichloroisonicotinic acid (500 mg, 2.60 mmol) in anhydrous DMA (4 ml). The mixture was stirred for 10 minutes after which 2-morpholin-4-yl-ethylamine (420 μl, 2.86 mmol) was added. The mixture was stirred at room temperature for 12 h and the mixture was partitioned between EtOAc and water. The EtOAc layer was washed well with water, dried over sodium sulphate and concentrated in vacuo to give the title compound as an oil (830 mg).

Workup

  1. additionwas added
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe EtOAc layer was washed well with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ab605f0abae4b7d852e4c8e1465e2fa
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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