Sodium Carbonate → HCID 59277585, compound

HRID 1362461Notes

Reaction equation

HRID 1362461 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:18])[C@H:15]([CH3:17])[NH2:16])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1.CN(C=O)C>[C:8]([C:7]1[C:2]([NH:16][C@@H:15]([CH3:17])[C:14]([O:13][CH2:11][CH3:12])=[O:18])=[N:3][CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 810792-ChloronicotinonitrileHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 59277585HCID 59277585, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-cyanopyridine (2 g, 14.4 mmol), L-alanine ethyl ester hydrochloride (3.3 g, 21.6 mmol), sodium carbonate (5.9 g, 43 mmol) in pyridine (1.75 mL) and DMF (20 mL) was heated to 125° C. for 36 h. The reaction was quenched with water and extracted with ethyl acetate (3×15 mL). The product was purified using column chromatography (10% MeOH in CH2Cl2) to yield a pale yellow solid (720 mg, 23%): 1H NMR (400 MHz, CDCl3) δ 8.26 (d, J=4.8 Hz, 1H), 7.69-7.67 (m, 1H), 6.67-6.64 (m, 1H), 4.77-4.74 (m, 1H), 4.23-4.19 (m, 2H), 1.54 (d, J=7.2 Hz, 3H), 1.30-1.26 (m, 3H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. customThe product was purified

Sources & evidence

ORD record
ord-abd5d3283cce4aca8524dd91e2f68a8d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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