Sodium ethoxide → HCID 178517571, compound

HRID 880810Notes

Reaction equation

HRID 880810 reaction equation
Cl.[F:2][C:3]([F:13])([F:12])[C:4]1[N:5]=[C:6]([C:9]([NH2:11])=[NH:10])[S:7][CH:8]=1.C([O:16][C:17]([C:19]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:20][O-])=O)C.[Na+].CC[O-].[Na+]>CCO>[O:22]([C:19]1[C:17]([OH:16])=[N:10][C:9]([C:6]2[S:7][CH:8]=[C:4]([C:3]([F:2])([F:12])[F:13])[N:5]=2)=[N:11][CH:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 66730292HCID 66730292, compoundHCID 667304744-(Trifluoromethyl)thiazole-2-carboximidamide hydrochloride

Product 1

HCID 178517571HCID 178517571, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of compound 282 (280 mg, 1 eq.) in dry EtOH (6 mL) was added compound 291 (1.38 g, 5 eq.) under nitrogen, followed by NaOEt (165 mg, 1 eq.). The reaction mixture was stirred at 90° C. for 2 hrs. EtOH was evaporated and a DCM/water mixture was added. Aqueous layer was acidified to pH 5 with aqueous 1N HCl and was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo, and purified by chromatography on silica gel (DCM/MeOH) to yield compound A1l as a beige oil in 81% yield. MS (ESI, EI+): m/z=340 (MH+).

Workup

  1. customEtOH was evaporated
  2. additiona DCM/water mixture was added
  3. extractionwas extracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography on silica gel (DCM/MeOH)
  8. customto yield compound A1l as a beige oil in 81% yield

Sources & evidence

ORD record
ord-100856ed74a443659784365fc801529d
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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