Sodium Hydroxide → HCID 66855058, compound

HRID 1530000Notes

Reaction equation

HRID 1530000 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29]C(=O)C)[CH:24]=3)[S:10][C:11]=2[C:12]2[N:16]=[CH:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.CO.[OH-].[Na+]>C(OCC)(=O)C.O>[C:1]1([C:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=3)[S:10][C:11]=2[C:12]2[N:16]=[CH:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 66855410HCID 66855410, compound

Product 1

HCID 66855058HCID 66855058, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To N-(4-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyridin-2-yl)acetamide (2.0 g, 4.4 mmol) prepared in the same manner as above in a mixed solvent (88 mL) of tetrahydrofuran/methanol (1:1) was added 1N aqueous sodium hydroxide solution (44 mL, 44.0 mmol), and the mixture was stirred at 60° C. for 3 hr. The reaction solution was cooled to room temperature, and diluted with ethyl acetate (300 mL) and water (150 mL). The aqueous layer was separated and extracted with ethyl acetate (200 mL), and the combined organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained solid was washed with diethyl ether (25 mL) and hexane (25 mL) to give the title compound (1.6 g, 87%) as a pale-yellow solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (200 mL)
  4. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe obtained solid was washed with diethyl ether (25 mL) and hexane (25 mL)

Sources & evidence

ORD record
ord-4c83019a86c94f3aa398751e219c894a
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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