Methyl 2-chloronicotinate → HCID 178498114, compound

HRID 1842503Notes

Reaction equation

HRID 1842503 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:7]=3[N:6]=2)[CH2:2]1.[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1Cl>CN(C=O)C.O>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[N:1]1[CH2:4][CH:3]([C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:7]=3[N:6]=2)[CH2:2]1

Participants

5

Reactant 2

HCID 819931Methyl 2-chloronicotinateHCID 178477890HCID 178477890, compound

Product 1

HCID 178498114HCID 178498114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-azetidin-3-yl-5-chloro-1H-benzoimidazole (as prepared according to Preparation 5 above) (3.2 g, 15.4 mmol) and 2-chloro-nicotinic acid methyl ester (1.78 g, 10.4 mmol) was dissolved in DMF (10 mL) and heated to 100° C. for 2 h. The mixture was diluted with water (10 mL), and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo to afford the product as yellow solid.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1d8bce7e04ae432b9a5263b66869b43e
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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