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

HRID 77785Notes

Reaction equation

HRID 77785 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-e3def6ea8e504ec09340212c25928a42
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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