Water → HCID 21109713, compound

HRID 1766455Notes

Reaction equation

HRID 1766455 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[C:7](Cl)=[N:6][CH:5]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[OH-].[K+]>CS(C)=O.CN(C=O)C.C(O)(=O)C>[CH2:13]([NH:20][C:7]1[C:8]([Br:10])=[CH:9][C:4]([C:3]([OH:2])=[O:12])=[CH:5][N:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 14797Potassium HydroxideHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 21109713HCID 21109713, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 0.3 g (1.27 mmol) 5-bromo-6-chloro-nicotinic acid methylester and 0.34 g (3.17 mmol) benzylamine in 0.4 mL DMSO was heated to 160° C. in the microwave for 4 min. 0.6 mL water and 0.4 mL 5N KOH aq was added and heated to 160° C. in the microwave for 2 min. Acetic acid and DMF was added and the mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 0.195 g (50%) of the title compound. MS (m/e): 307.1 (M−H).

Workup

  1. temperatureheated to 160° C. in the microwave for 2 min
  2. customthe mixture was purified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile/water/HCOOH
  5. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-2c87b990f74c485ab5f4ebd9bb9a00e2
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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