m-Anisoyl chloride → HCID 46843298, compound

HRID 533742Notes

Reaction equation

HRID 533742 reaction equation
[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[C:24](Cl)(=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1.Cl.CCOCC>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][N:10]([C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=4)=[O:33])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843298HCID 46843298, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (50 mg, 0.24 mmol) and DIEA (0.05 mL, 0.29 mmol) were dissolved in THF (2 mL). m-Anisoyl chloride (0.04 mL, 0.29 mmol) was added dropwise, and the reaction solution was stirred at room temperature for 1 h. The crude reaction mixture was concentrated, and converted to the HCl salt by dissolving the crude material in MeOH (2 ml) and adding 1 M HCl/ether (2 equiv). The resulting solution was refrigerated overnight. The resulting precipitate was filtered and dried under vacuum to provide 25 (50 mg, 55% yield) as an off white solid. LC-MS (M+H=342, obsd.=342).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. dissolutionby dissolving the crude material in MeOH (2 ml)
  4. waitThe resulting solution was refrigerated overnight
  5. filtrationThe resulting precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b90140e8f7bb43298206546181e026f5
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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