Triethylamine → HCID 21257617, compound

HRID 2306107Notes

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, compound

Procedure

2″,7″-[Bis-(4β-N-podophyllotoxin)] diaminoflourene (8a) was prepared by the same method described earlier, employing 2,7-diamino flourene (135 mg, 0.5 mmol), Bu4N+I−(185 mg, 0.5 mmol) and Et3N (150 mg, 1.5 mmol) and 4β-bromo podophyllotoxin (476 mg, 1.0 mmol) to give 8a in 75% yield. Spectral data: 1H NMR (CDCl3); 7.39-7.50 (d, 2H), 6.82 (S, 2H), 6.68 (S, 2H), 6.45-6.58 (br, 4H), 6.31 (S, 4H), 5.92-6.01 (ABq, 4H), 4.71 (br, 2H), 4.60 (d, 2H), 4.38-4.48 (t, 2H), 4.00-4.13 (t, 2H), 3.80 (d, 18H), 3.10-3.22 (dd, 2H), 2.90-3.10 (m 2H); FAB MS: mn/z 988 (M+); mp. 215-218° C.

Sources & evidence

ORD record: ord-2a043aca9ce04343801482043646e694
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441198B1

Reaction notes

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