Triethylamine → HCID 68629838, compound

HRID 1847282Notes

Reaction equation

HRID 1847282 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:20]([CH3:23])=[N:21][S:22][C:10]=2[C:9]=1[OH:24])=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11]2[C:20]([CH3:23])=[N:21][S:22][C:10]=2[C:9]=1[O:24][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 68630592HCID 68630592, compound

Product 1

HCID 68629838HCID 68629838, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-Hydroxy-3-methyl-4-phenyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester (1.15 mmol), trimethylacetyl chloride (1.39 mmol), Et3N (1.74 mmol), and CH2Cl2 (5.7 mL) was stirred at r.t. for 2 h. The mixture was then quenched with water and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2 gave the title compound (392.8 mg) as a colorless oil: MS (m/z) 427.2 (M+1).

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-24c3abac32334a979ea4c68fed5649ef
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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