Triethylamine → HCID 86649351, compound

HRID 1847254Notes

Reaction equation

HRID 1847254 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10]([I:12])[N:11]=1)=[O:5])[CH3:2].[CH3:24][C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:23][C:26](=[O:27])[C:25]([CH3:30])([CH3:29])[CH3:24])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10]([I:12])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 136344019HCID 136344019, compound

Product 1

HCID 86649351HCID 86649351, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chloro-phenyl)-4-hydroxy-7-iodo-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (0.47 mmol) in CH2Cl2 (2.38 mL) was added trimethylacetyl chloride (0.57 mmol) and Et3N (0.71 mmol). The reaction mixture was stirred at r.t. for 2 h before the mixture was filtered. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2, gave the title compound (225 mg) as a white solid: MS (m/z) 544.9 (M+1).

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by flash column chromatography on silica gel
  4. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-c60c7705b66a4b6db4452e3983860081
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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