Pyridine → HCID 73062791, compound

HRID 1393000Notes

Reaction equation

HRID 1393000 reaction equation
[CH3:1][N:2]1[CH2:6][C:5]23[CH:11]([CH2:12][CH2:13][CH:4]2[CH2:3]1)[C:10]1[CH:14]=[CH:15][C:16]([C:18]2[CH:19]=[C:20]([C:24](=O)[CH3:25])[CH:21]=[CH:22][CH:23]=2)=[CH:17][C:9]=1[CH2:8][CH2:7]3.Cl.[NH2:28][OH:29].N1C=CC=CC=1>C(O)C>[CH3:1][N:2]1[CH2:6][C:5]23[CH:11]([CH2:12][CH2:13][CH:4]2[CH2:3]1)[C:10]1[CH:14]=[CH:15][C:16]([C:18]2[CH:19]=[C:20]([C:24](=[N:28][OH:29])[CH3:25])[CH:21]=[CH:22][CH:23]=2)=[CH:17][C:9]=1[CH2:8][CH2:7]3

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 56675065HCID 56675065, compound

Product 1

HCID 73062791HCID 73062791, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[3-(8-Methyl-5,6,6a,7,8,9,10,11-octahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrol-2-yl)-phenyl]-ethanone (Example 2)(10.0 mg, 0.028 mmol), hydroxylamine hydrochloride (2.9 mg, 0.042 mmol), and pyridine (226 μL, 0.28 mmol) were heated in ethanol (1 mL) at 80° C. for 3 h. The mixture was quenched with water (1 mL), extracted with CH2Cl2 (2 mL×4). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane, providing 1.9 mg (18.3%) of the title compound.

Workup

  1. customThe mixture was quenched with water (1 mL)
  2. extractionextracted with CH2Cl2 (2 mL×4)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4d6cde531c6941f08c51859171e625e1
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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