Sodium Bicarbonate → HCID 178508267, compound

HRID 875993Notes

Reaction equation

HRID 875993 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH2:15])[N:13]=[CH:14][C:9]=3[C:8]3[CH:16]=[CH:17][C:18]([O:20]C)=[N:19][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>Cl>[NH2:15][C:12]1[N:13]=[CH:14][C:9]2[C:8]3[CH:16]=[CH:17][C:18]([OH:20])=[N:19][C:7]=3[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58299662HCID 58299662, compound

Product 1

HCID 178508267HCID 178508267, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
140 °C

Procedure

Compound 268 (150 mg, 529 μmol) was dissolved in conc. hydrochloric acid (2 mL). The reaction was heated with microwave energy (300 W) for 40 min. at 140° C. The resulting solution was added to aqueous NaHCO3 (20 mL, 50% sat.) and extracted with dichloromethane+10% methanol (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give an orange tar. Silica gel chromatography (gradient elution hexanes+2.5% TEA/0-100% ethyl acetate+2.5% TEA) afforded compound 272 as a tan solid, 120 mg (84%).

Workup

  1. extractionextracted with dichloromethane+10% methanol (3×30 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give an orange tar
  5. washSilica gel chromatography (gradient elution hexanes+2.5% TEA/0-100% ethyl acetate+2.5% TEA)

Sources & evidence

ORD record
ord-19a8e5487ba648e593b0dd4fd211ae0a
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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