Benzoyl chloride → HCID 46843286, compound

HRID 533736Notes

Reaction equation

HRID 533736 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:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][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]=[CH:27][CH:26]=4)=[O:31])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843286HCID 46843286, compoundYield 79%

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). Benzoyl chloride (0.03 ml, 0.29 mmol) was added dropwise and the reaction 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 19 (33 mg, 40% yield) as a pale yellow solid. LC-MS (M+H=312, obsd.=312).

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-b4f504b2052b49d9b892e7e1e22f8332
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

Loading…