Acetic Acid → HCID 67458316, compound

HRID 1944288Notes

Reaction equation

HRID 1944288 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.N1C=CC=CC=1.[CH2:38]([S:40](Cl)(=[O:42])=[O:41])[CH3:39].C(O)(=O)C>ClCCl.O>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:29])[F:30])=[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][S:40]([CH2:38][CH3:39])(=[O:42])=[O:41])=[CH:24][CH:25]=1)[C:10]([CH2:17][CH3:18])=[N:11]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 67459140HCID 67459140, compound

Product 1

HCID 67458316HCID 67458316, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [3-(4-aminobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.051 g), pyridine (0.019 mL) and dichloromethane (0.5 mL) at 0° C. was treated with ethanesulfonyl chloride (0.013 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane and water, and then acidified by the addition of glacial acetic acid. The organic phase was dried over magnesium sulfate, and then concentrated under reduced pressure to afford title compound as a yellow gum (0.051 g).

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c9111abd00a43b68daf3c57b3d4da2a
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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