Diisopropylethylamine → HCID 46843296, compound

HRID 533741Notes

Reaction equation

HRID 533741 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[C:26]([O:31][CH3:32])=[CH:27][CH:28]=[CH:29][CH:30]=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]=[CH:27][C:26]=4[O:31][CH3:32])=[O:33])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 889692-Methoxybenzoyl chlorideHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843296HCID 46843296, compoundYield 105.7%

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). o-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 24 (48 mg, 53% 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-101f82865d1146b1ad70509581fd9b35
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

Loading…