1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-chloro-6-methyl-N-(1-methyl-1-phenylethyl)nicotinamide

HRID 21343Notes

Reaction equation

HRID 21343 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8](C)=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12]CN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:34]([NH2:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:36])[CH3:35]>CN(C=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:43][C:34]([CH3:36])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:35])=[O:6]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 123877302-Chloro-5-methylnicotinic acid

Product 1

HCID 866283402-chloro-6-methyl-N-(1-methyl-1-phenylethyl)nicotinamideYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 2-chloro-5-methylnicotinic acid (2.00 g, 11.7 mmol) was dissolved in DMF (40 mL), and the solution was treated with EDCI (3.35 g, 17.5 mmol), HOBT monohydrate (890 mg, 5.83 mmol) and cumylamine (3.40 mL, 23.3 mmol). The mixture was added with water. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 2-chloro-6-methyl-N-(1-methyl-1-phenylethyl)nicotinamide (2.09 mg, yield 62%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-9127249f319244ed9a3d3dc663bb9562
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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