Sodium Bicarbonate → HCID 58631219, compound

HRID 1824283Notes

Reaction equation

HRID 1824283 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[OH:18])[CH:5]=[N:4][CH:3]=1.C[O-].[Na+].[C:22]([O-])(O)=[O:23].[Na+]>CO.CCOC(C)=O>[CH3:22][O:23][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[OH:18])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium Methoxide3×HCID 58583287HCID 58583287, compound

Product 1

HCID 58631219HCID 58631219, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,2S)-1-[(6-chloropyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol (2 g, 7.6 mmol) in MeOH (26 mL) was added a solution of NaOMe (1.3 g, 23 mmol) in MeOH (40 mL). The mixture was heated at reflux for 24 hr. Additional NaOMe (1.3 g) was added. Continue heating at reflux for 24 hr, and then add additional NaOMe (1.3 g). Continue heating at reflux for 24 hr and cool to rt. Dilute with EtOAc and was with sat. aq. NaHCO3. The solids were removed by filtration. Separate phases and wash organic extract with additional sat. aq. NaHCO3. Dry organic extracts over MgSO4, filter and concentrate. Purify by biotage MPLC (90 g column, 25% ethyl acetate/hexanes) to afford 1.4 g (71%) of (1R,2S)-1-[(6-methoxypyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol as an oil: 1H NMR (CDCl3) δ 3.04–3.08, 3.23–3.29, 3.91, 4.75–4.78, 5.18, 5.42–5.45, 7.25–7.34, 7.57–7.61; MS (ESI+) for C14H15N3O2 m/z 258 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hr
  3. temperatureContinue heating
  4. temperatureat reflux for 24 hr
  5. temperatureContinue heating
  6. temperatureat reflux for 24 hr
  7. customThe solids were removed by filtration
  8. washSeparate phases and wash organic
  9. extractionextract with additional sat. aq. NaHCO3
  10. filtrationDry organic extracts over MgSO4, filter
  11. concentrationconcentrate
  12. customPurify by biotage MPLC (90 g column, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ff2110594123498096202955682f8f0e
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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