Sodium ethoxide → HCID 178515749, compound

HRID 530761Notes

Reaction equation

HRID 530761 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8](=[NH:10])[NH2:9])[S:6][CH:7]=1.CC[O-].[Na+].O=[C:18]([C:25]1[S:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=1)[CH2:19][C:20](OCC)=[O:21]>C(O)C>[F:12][C:2]([F:1])([F:11])[C:3]1[N:4]=[C:5]([C:8]2[N:9]=[C:20]([OH:21])[CH:19]=[C:18]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[N:29]=3)[N:10]=2)[S:6][CH:7]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 582827454-(Trifluoromethyl)thiazole-2-carboximidamideHCID 68160095Ethyl 3-oxo-3-(4-(trifluoromethyl)thiazol-2-yl)propanoate

Product 1

HCID 178515749HCID 178515749, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound 27 (0.43 mmol) and NaOEt (2.15 mmol) in ethanol (2 mL) was added compound 28 (0.43 mmol). The reaction mixture was stirred at 100° C. overnight. The solvent was evaporated and water and AcOEt were added. The aqueous layer was acidified to pH˜4-5 by addition of 2.5M HCl. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: DCM/MeOH 0 to 5%) to give compound 29 as a beige solid in 11% yield. MS (ESI, EI−): m/z=396.91 (MH−).

Workup

  1. customThe solvent was evaporated
  2. additionwater and AcOEt were added
  3. additionThe aqueous layer was acidified to pH˜4-5 by addition of 2.5M HCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluent: DCM/MeOH 0 to 5%)

Sources & evidence

ORD record
ord-bb479b9b8d194a3b9b97e35946f2b141
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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