1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53416990, compound

HRID 1697061Notes

Reaction equation

HRID 1697061 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 53416990HCID 53416990, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-6-methyl-nicotinic acid (2 g, 12 mmol), N,O-dimethylhydroxylamine hydrochloride (1.14 g, 12 mmol), EDCI (2.68 g, 14 mmol), HOBt (81 mg, 16 mmol) and DIPEA (1 mL) in DCM (100 mL) was stirred at RT overnight. The reaction mixture was then partitioned between water and DCM, the organic layer separated, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, gradient from 0 to 25% in 25 minutes) to afford 2.4 g of 2-chloro-N-methoxy-6,N-dimethyl-nicotinamide as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between water and DCM
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (EtOAc/hexane, gradient from 0 to 25% in 25 minutes)

Sources & evidence

ORD record
ord-d8f418b67504429e8fdc6c256cf8f9f2
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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