Ethyl Acetate → HCID 9972278, compound

HRID 1836447Notes

Reaction equation

HRID 1836447 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][N:7]=1.[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 18619165HCID 18619165, compound

Product 1

HCID 9972278HCID 9972278, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-amino-pyridin-2-yloxy)-acetic acid methyl ester (0.16 g, 0.88 mmol) in dichloromethane (5 mL) was added 4-fluorobenzoyl chloride (0.11 mL, 0.97 mmol) and N,N-diisopropylethylamine (0.33 mL, 1.9 mmol). After 24 h the reaction was poured into ethyl acetate, washed with water, and dried over sodium sulfate. Removal of the solvent gave a white solid that was purified by trituation using ethyl acetate/hexanes to give the titled product 0.18 g (67%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s,1H); 8.40 (m, 1H); 8.03 (m, 3H); 7.35 (m, 2H); 6.92 (m, 1H); 4.87 (m, 2H); 3.64 (m, 3H).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvent
  4. customgave a white solid
  5. customthat was purified by trituation

Sources & evidence

ORD record
ord-5113300edc5c4aa190195c2b543e2fa5
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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