Dicyclohexylcarbodiimide → (6-chloro-5-methylpyridin-3-yl)-N-(5-(pyridazin-3-yl)pyridin-2-yl)acetamide

HRID 1036222Notes

Reaction equation

HRID 1036222 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=2)[N:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:15]3[N:14]=[N:13][CH:18]=[CH:17][CH:16]=3)=[CH:24][N:23]=2)=[O:11])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 552673572-(6-Chloro-5-methylpyridin-3-yl)acetic acidHCID 584476635-(Pyridazin-3-yl)pyridin-2-amine

Product 1

HCID 86657954(6-chloro-5-methylpyridin-3-yl)-N-(5-(pyridazin-3-yl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 86-7 (241 mg, 1.3 mmol), 5-(pyridazin-3-yl)pyridin-2-amine 145-3 (224 mg, 1.3 mmol), 1,3-dicyclohexylcarbodiimide (325 mg, 1.6 mmol) and 4-(dimethylamino)pyridine (26 mg, 0.26 mmol) in DMF (6 mL) was stirred at room temperature for 10 hours. The reaction mixture was filtered to remove the solid and the filtrate was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(pyridazin-3-yl)pyridin-2-yl)acetamide 145-4 as pale yellow solid. MS m/z 340.2 (M+1)

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the solid
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-e6c278275ff043adacf96bf899d69bc5
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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