2-Chloroaniline → HCID 24771611, compound

HRID 645363Notes

Reaction equation

HRID 645363 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ONN1C=CN=N1.C(N(CC)C(C)C)(C)C.[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59](O)=[O:60])[N:58]=2)[CH:55]=1>CN(C)C=O.C(=O)([O-])O.[Na+]>[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59]([NH:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[Cl:1])=[O:60])[N:58]=2)[CH:55]=1

Participants

8

Reactant 5

HCID 72402-ChloroanilineHCID 81531DiisopropylethylamineHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136346319HCID 136346319, compound

Product 1

HCID 24771611HCID 24771611, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

54 μl of 2-chloroaniline, 211 mg of HATU, 75 mg of 1-hydroxyaminotriazole and 237 μl of N,N-diisopropylethylamine are added to a solution of 100 mg of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 1 ml of N,N-dimethylformamide. The reaction mixture is heated at 70° C. for 16 hours, diluted with a saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. The residue is purified by flash chromatography on silica, elution being carried out with a hexane/ethyl acetate 70/30 mixture to give 62 mg of 6-chloro-N-(2-chlorophenyl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined organic phases are dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash chromatography on silica, elution

Sources & evidence

ORD record
ord-e642ba07940644169aad1ad2344d58f2
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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