Triethylamine → HCID 21257617, compound

HRID 2306109Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](N)=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CC[N:18](CC)CC>>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[C:3]=1[NH2:18]

Participants

Reactant 2

HCID 8471Triethylamine

HCID 106792,7-Diaminofluorene

Product 1

HCID 21257617HCID 21257617, compoundYield 70%

Procedure

2″,7″-[Bis-(4′-O-demethylA4β-N-4-desoxypodophyllotoxin)] diamino flourene (8b) was prepared according to the procedure described for the earlier compounds, employing 2,7-diamino flourene (135 mg, 0.5 mmol), Bu4N+I−(185 mg, 0.5 mmol), Et3N (150 mg, 1.5 mmol) and 4′-O-demethyl-4β-bromo podophyllotoxin (462 mg, 1.0 mmol) to give the product in 70% yield. Spectral data: 1H NMR (CDCl3); 7.39-7.45 (d, 2H), 6.78 (S, 2H), 6.66 (S, 2H), 6.50 (S, 2H), 6.43-6.48 (d, 2H), 6.30 (S, 4H), 5.92-6.00 (ABq, 4H), 5.33 (S, 2H), 4.70 (br, 2H), 4.55-4.61 (d, 2H), 4.334.45 (t, 2H), 3.97-4.10(t,2H), 3.79 (S, 6H), 3.08-3.20 (dd, 2H), 2.90-3.08 (m, 2H); FAB MS: m/z 960 (M+); mp. 240-243° C.

Workup

customto give the product in 70% yield

Sources & evidence

ORD record: ord-6eb6ebe073804d6a8ba8cc19af9c3833
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441198B1

Reaction notes

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