Sodium ethoxide → HCID 178517571, compound

HRID 925994Notes

Reaction equation

HRID 925994 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 AI1 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 AI1 as a beige oil in 81% yield

Sources & evidence

ORD record
ord-eea5fadf217d4d56832743498f3a0ded
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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