Hydrochloric Acid → HCID 67118526, compound

HRID 1189022Notes

Reaction equation

HRID 1189022 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:19]=2)[NH:16][C:15]([C:24]2[S:25][CH:26]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:27][N:28]=2)=[CH:14]3)=[CH:6][CH:5]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:19]=2)[NH:16][C:15]([C:24]2[S:25][CH:26]([CH2:29][C:30]([OH:32])=[O:31])[CH2:27][N:28]=2)=[CH:14]3)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70963867HCID 70963867, compound

Product 1

HCID 67118526HCID 67118526, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl {2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(1-methylethoxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (680 mg), tetrahydrofuran (5 mL), ethanol (5 mL) and 1M aqueous sodium hydroxide solution (5 mL) was stirred at 50° C. for 30 min, and then cooled to room temperature. Water and 1M hydrochloric acid (5 mL) were added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound (600 mg, 94%) as a yellow amorphous solid. MS 456 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68918f7178214d19abbff55d04034b4b
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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