Triethylamine → 3-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester

HRID 217360Notes

Reaction equation

HRID 217360 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([NH2:17])[CH:5]=1.CCN(CC)CC.[C:26](Cl)(=[O:30])[CH:27]([CH3:29])[CH3:28]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([NH:17][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 578515533-Amino-5-(5-chloro-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 578514303-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl esterYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-5-(5-chloro-pyridin-2-yl)-benzoic acid methyl ester (1.5 g, 5.71 mmol, from Preparation 2) and Et3N (2.39 mL, 17.13 mmol) were dissolved in 30 mL methylene chloride, and isobutyryl chloride (72 mL, 6.85 mmol) was added. The reaction mixture was stirred at room temperature for two hours, and then was partitioned between water and methylene chloride. The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to give 1.29 g of 3-(5-chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester, MS (M+H)=333.

Workup

  1. customwas partitioned between water and methylene chloride
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04f77ca9f92b460588a1e897cc45b381
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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