Sodium Carbonate → HCID 68779363, compound

HRID 1876816Notes

Reaction equation

HRID 1876816 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[BH3-]C#N.[Na+].[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([N:24]2[CH:33]3[CH:28]([CH2:29][CH2:30][CH2:31][CH:32]3[N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[NH:27][CH2:26][CH2:25]2)=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20].C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([N:24]2[CH:33]3[CH:28]([CH2:29][CH2:30][CH2:31][CH:32]3[N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:27]([CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:26][CH2:25]2)=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 142732-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Product 1

HCID 68779363HCID 68779363, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Pyridine-2-carbaldehyde (268 mg, 2.5 mmol) was dissolved in MeOH (5 ml) and NaBH3CN (157 mg, 2.5 mmol) was added. The pH was adjusted to 5 with concentrated acetic acid. 2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (98 mg, 0.25 mmol), dissolved in MeOH (15 ml), was then added to the mixture and the mixture was stirred at room temperature overnight. After addition of saturated Na2CO3 solution (15 ml), the mixture was stirred at room temperature for 15 minutes. The precipitate formed was filtered off. The aqueous phase of the filtrate was extracted five times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was purified four times by flash chromatography (in each case Ø 2 cm, l=15 cm, V=5 ml; 1. CH2Cl2/MeOH/NH3 9.5:0.5:0.1, 2. CH2Cl2/MeOH/NH3 9.5:0.5:0.1, 3. CH2Cl2/MeOH/NH3 9.75:0.25:0.15, 4. CH2Cl2/MeOH/NH3 9.5:0.5:0.15). The crude product was then purified by preparative HPLC (as described under Example 14 in MeOH/H2O/Et2NH 80:20:0.1). MeOH was evaporated off from the product fraction, the aqueous phase was extracted by shaking three times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated. A yellowish resin was isolated.

Workup

  1. additionwas then added to the mixture
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. extractionThe aqueous phase of the filtrate was extracted five times with CH2Cl2
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residue was purified four times by flash chromatography (in each case Ø 2 cm, l=15 cm, V=5 ml
  9. customThe crude product was then purified by preparative HPLC (as described under Example 14 in MeOH/H2O/Et2NH 80:20:0.1)
  10. customMeOH was evaporated off from the product fraction
  11. extractionthe aqueous phase was extracted
  12. stirringby shaking three times with CH2Cl2
  13. dry with materialthe combined organic phases were dried over Na2SO4
  14. customevaporated
  15. customA yellowish resin was isolated

Sources & evidence

ORD record
ord-9a8567a4cb0f498f9eb7d1ff959f6f4e
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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