Sodium ethoxide → HCID 57652832, compound

HRID 2355065Notes

Reaction equation

HRID 2355065 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:14][CH2:13][C@H:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:11]2)=[N:7][CH:6]=1)[NH2:4].[CH3:26][CH2:27][O-].[Na+]>CCO.CCOC(C)=O.O>[CH3:26][C:27]1[O:1][N:2]=[C:3]([C:5]2[S:9][C:8]([N:10]3[CH2:14][CH2:13][C@H:12]([O:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])[CH2:11]3)=[N:7][CH:6]=2)[N:4]=1

Participants

6

Reactant 2

HCID 2723922Sodium ethoxideHCID 86629249HCID 86629249, compound

Product 1

HCID 57652832HCID 57652832, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N′-hydroxy-2-{(3S)-3-[2-(trifluoromethyl)phenoxy]-pyrrolidin-1-yl}-1,3-thiazole-5-carboximidamide (410 mg, 1.1 mmol) in EtOH (3 mL) and EtOAc (5 mL) was added NaOEt (1.7 mL, 4.4 mmol, 25 wt. %) at rt. The mixture was heated at 80° C. for 30 min. After cooling to rt, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed with water, dried (Na2SO4) and concentrated. Combi-Flash chromatography (10 g, 50-100% EtOAc in hexanes in 20 min, 35 mL/min, 15 mL/fraction) gave the title compound after trituration with Et2O-hexanes (1:1). 1H NMR (400 MHz, acetone-d6): δ 7.81 (s, 1 H), 7.71-7.65 (m, 2 H), 7.41 (d, 1 H), 7.17 (t, 1 H), 5.52 (s, 1 H), 3.98 (m, 1 H), 3.84-3.67 (m, 3 H), 2.61 (s, 3H), 2.60-2.43 (m, 2 H). MS (+ESI) m/z 397 (MH+).

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b5a69439d3f42a6ba2853ccc48f8ae0
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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