Aniline → 7-Phenyliminomethylcamptothecin

HRID 2212807

Reaction equation

HRID 2212807 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:28])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[C:14](=[C:15]([CH:26]=O)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Yb]>C(Cl)Cl>[CH3:1][CH2:2][C@@:3]1([OH:28])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[C:14](=[C:15]([CH:26]=[N:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

Participants

5

Reactant 3

HCID 6115AnilineHCID 23992YtterbiumHCID 1498761H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, (S)-

Product 1

HCID 98684337-PhenyliminomethylcamptothecinYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

100 mg (0.26 mmoles) of 7-formylcamptothecin, dissolved into 20 ml of methylene chloride, and 25 μl (0.26 mmoles) of aniline, dissolved into 0.5 ml of methylene chloride, were added to a suspension of ytterbium triphlate (16.5 mg. 0.026 mmoles, 10% mol) in 5 ml of methylene chloride containing MS 4A and were left 3.5 hours under stirring at room T, then the solvent was evaporated under vacuum. The product was purified by means of flash chromatography on silica gel using a mixture of methylene chloride/methanol 98/2 as eluant. 60 mg of a yellow solid were obtained.

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe product was purified by means of flash chromatography on silica gel using
  3. additiona mixture of methylene chloride/methanol 98/2 as eluant

Sources & evidence

ORD record
ord-fe2875e78d884eb89e45d3ccbabf7e39
Source dataset
uspto-grants-2006_09
Patent number
US07105492B2

Linked notes

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