Ethylenediamine → HCID 59734937, compound

HRID 550393Notes

Reaction equation

HRID 550393 reaction equation
[O:1]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[C:23]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=1)[CH2:19]2.C(C(O)=O)(F)(F)F.C(N)CN>C(Cl)Cl.C([O-])(O)=O.[Na+]>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[C:23]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=1)[CH2:19]2

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 59734933HCID 59734933, compound

Product 1

HCID 59734937HCID 59734937, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (±)-methyl 2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate (3.65 g, 8.60 mmol) in CH2Cl2 (80 mL) was added CF3CO2H (40 mL, 52 mmol) and the resulting mixture was stirred at ambient temperature for 18 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL) and treated with ethylene diamine (2.3 mL, 34.4 mmol). The reaction mixture was stirred at ambient temperature for 18 h, then diluted with saturated aqueous NaHCO3 (50 mL). The organic layer was removed and the aqueous layer was extracted further with CH2Cl2 (2×100 mL). The combined organic layers were washed with brine (50 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with CH2Cl2:MeOH—97:3, to give methyl 2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate as a tan solid. This solid was dissolved in MeOH (22 mL) and 1 N sodium hydroxide (25.4 mL, 25.4 mmol) was added. The reaction mixture was heated at 60° C. for 18 h then allowed to cool. The mixture was acidified by addition of 6 N HCl, and the resulting precipitate was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound as an off-white solid. MS: m/z=281 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 18 h
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted further with CH2Cl2 (2×100 mL)
  6. washThe combined organic layers were washed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by silica gel chromatography
  11. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-0b3775f18c494f858092192c69c69529
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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