Acetic Acid → HCID 23581951, compound

HRID 551104Notes

Reaction equation

HRID 551104 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:24][C:13]1=[CH:14][C:15]3[N:16]=[C:17]([CH:22]=O)[CH:18]=[N:19][C:20]=3[CH:21]=[C:12]1[CH2:11]2.[NH:25]1[C:35]2[C:36]3[CH:27]([CH2:28][C:29](=[O:37])[NH:30][C:31]=3[CH:32]=[CH:33][CH:34]=2)[CH2:26]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:37]=[C:29]1[CH2:28][CH:27]2[CH2:26][N:25]([CH2:22][C:17]3[CH:18]=[N:19][C:20]4[CH:21]=[C:12]5[CH2:11][C:3]6([C:4]7[C:5](=[N:6][CH:7]=[CH:8][CH:9]=7)[NH:10][C:2]6=[O:1])[CH2:24][C:13]5=[CH:14][C:15]=4[N:16]=3)[C:35]3[C:36]2=[C:31]([CH:32]=[CH:33][CH:34]=3)[NH:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 104421921,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-oneHCID 86629745HCID 86629745, compound

Product 1

HCID 23581951HCID 23581951, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of (±)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoxaline-7,3′-pyrrolo[2,3-b]pyridine]-2-carbaldehyde from Step B (16 mg, 0.051 mmol), 1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one, enantiomer B (11 mg, 0.061 mmol, described in Intermediate 19), and AcOH (0.029 mL, 0.51 mmol) in DCE (0.4 mL) was added sodium triacetoxyborohydride (16 mg, 0.076 mmol) and the mixture was stirred for 4 h at ambient temperature. The solvent was removed in vacuo and the residue was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Saturated aqueous NaHCO3 (1 mL) was added to the tubes in the fraction collector in order to rapidly neutralize to eluted solvent. The pure, product-containing fractions were combined and extracted with CH2Cl2, and the organic extract was dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound. MS: m/z=475 (M+1). HRMS: m/z=475.1878; calculated m/z=475.1877 for C28H23N6O2.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by HPLC
  3. washeluting with a gradient of H2O
  4. additionSaturated aqueous NaHCO3 (1 mL) was added to the tubes in the fraction collector in order
  5. washto eluted solvent
  6. additionThe pure, product-containing fractions
  7. extractionextracted with CH2Cl2
  8. extractionthe organic extract
  9. dry with materialwas dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e4aff6169df4dccadf6d581e0a7ca19
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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