Diisopropylethylamine → 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide

HRID 1036189Notes

Reaction equation

HRID 1036189 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].[C:13]1([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:43][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=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:13]3[CH:14]=[CH:15][CH:16]=[C:17]([F:43])[CH:18]=3)=[CH:24][N:23]=2)=[O:11])=[CH:4][C:3]=1[CH3:12]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1050975-Phenyl-2-pyridinamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 552673572-(6-Chloro-5-methylpyridin-3-yl)acetic acid

Product 1

HCID 866579522-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 74-4 (222 mg, 1.2 mmol), 5-phenylpyridin-2-amine (336 mg, 1.8 mmol) and HATU (684 mg, 1.8 mmol) in DMF (5 mL) was added DIEA (600 μL, 3.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 aqueous solution, water and brine, dried over Na2SO4, and concentrated by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in dichloromethane to give 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide 74-5 as dark yellow solid. MS m/z 356.1 (M+1).

Workup

  1. washwashed with saturated NaHCO3 aqueous solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe crude product was purified by silica gel flash chromatography
  5. washeluted with 40% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-336d3c77fa4946d091d6a920db7fbeea
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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