Pyridine → N-(4-chlorophenyl)-1-pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 1246725Notes

Reaction equation

HRID 1246725 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH:11]=[C:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1.C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1>C(Cl)Cl.C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.O.CN(C=O)C>[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:13]([C:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH:11]=2)=[O:15])=[CH:31][CH:30]=1

Participants

10

Reactant 4

HCID 1049PyridineHCID 78124-ChloroanilineHCID 65578Oxalyl chlorideHCID 219047301-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid

Product 1

HCID 11324497N-(4-chlorophenyl)-1-pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxamide

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid (55.0 mg, 0.27 mmol) and a catalytic amount of DMF were combined in CH2Cl2 (1.5 mL) and treated with (COCl)2 (0.033 mL, 0.38 mmol). The mixture was stirred for 90 minutes, diluted with toluene (0.5 mL), and concentrated to dryness under reduced pressure. The residue in CH2Cl2 (1.5 mL) was treated with pyridine (0.033 mL, 0.41 mmol), catalytic amount of DMAP, and 4-chloroaniline (41.0 mg, 0.32 mmol). The mixture was stirred for 1 hour, diluted with water, and extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residure was purified by flash chromatography (15% ethyl acetate/CH2Cl2) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.35 (d, 2H), 7.51 (d, 2H), 7.39 (brs, 1H), 7.31 (d, 2H), 6.77 (sept, 1H), 6.54 (t, 1H), 4.43 (q, 2H), 4.03 (t, 2H), 2.58 (m, 2H); MS (m/z) 315.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residure was purified by flash chromatography (15% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-1fa1253543254d1f9473d75cf2d81740
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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