Ethyl Acetate → methyl 2-[(3-carbamoyl-5-chloro-2-iminopyridin-1(2H)-yl)methyl]-4-chlorobenzoate hydrobromide

HRID 1014018Notes

Reaction equation

HRID 1014018 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH2:23][Br:24])[CH:14]=1.C(OCC)(=O)C>CN(C=O)C>[BrH:24].[C:4]([C:3]1[C:2](=[NH:1])[N:10]([CH2:23][C:15]2[CH:14]=[C:13]([Cl:12])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH:9]=[C:8]([Cl:11])[CH:7]=1)(=[O:5])[NH2:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 20814722Methyl 2-(bromomethyl)-4-chlorobenzoateHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 66969549methyl 2-[(3-carbamoyl-5-chloro-2-iminopyridin-1(2H)-yl)methyl]-4-chlorobenzoate hydrobromideYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 3) A solution of 2-amino-5-chloronicotinamide (202 mg) and methyl 4-chloro-2-bromomethylbenzoate obtained in Step 2 (470 mg) in DMF (5 ml) was stirred overnight at 90° C. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were recrystallized from ethanol and ethyl acetate to give the title compound (78 mg).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customThe obtained crystals were recrystallized from ethanol and ethyl acetate

Sources & evidence

ORD record
ord-b16161c4d1ec4d5d994bc74175b31bc4
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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