1,2-Dichloroethane → ({3-[7-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionylamino}-methyl)-phosphonic Acid Diethyl Ester

HRID 853633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853633
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2[S:24][CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:38]([O:40][P:41]([CH2:46][NH2:47])(=[O:45])[O:42][CH2:43][CH3:44])[CH3:39].C(Cl)CCl.P(=O)([O-])OCN>C(Cl)Cl>[CH2:38]([O:40][P:41]([CH2:46][NH:47][C:27](=[O:29])[CH2:26][CH2:25][S:24][CH:8]1[C:9]2[C:10]([O:22][CH3:23])=[C:11]3[C:16](=[C:17]([OH:21])[C:18]=2[C:19](=[O:20])[N:7]1[CH2:6][C:5]1[CH:30]=[CH:31][C:2]([F:1])=[CH:3][CH:4]=1)[N:15]=[CH:14][CH:13]=[CH:12]3)(=[O:45])[O:42][CH2:43][CH3:44])[CH3:39]

Komponenten

6

Edukt 4

HCID 111,2-Dichloroethane2×HCID 2733594diethyl (aminomethyl)phosphonate oxalate saltHCID 100034673-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoic acidHCID 178514127HCID 178514127, Verbindung

Produkt 1

HCID 10483568({3-[7-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionylamino}-methyl)-phosphonic Acid Diethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 24 (15 mg, 0.035 mmol) in 0.35 mL of CH2Cl2 (0.35 mL) was added diethyl(aminomethyl)phosphonate oxalate (27 mg, 0.105 mmol), EDC (20 mg, 0.105 mmol) and TEA (15 μL, 0.105 mmol). The solution was stirred at room temperature for 1 day when the same amount of the aminomethyl phosphonate, EDC and TEA were added. The reaction was stirred for another day when complete conversion of starting materials to the desired product was observed by LCMS. The product 26 was purified by reverse phase HPLC using 5-95% A. Buffer A contained CH3CN-1% HOAc and buffer B was H2O-1% HOAc. 1H NMR (300 MHz, CDCl3) δ 1.33-1.40 (m, 6H), 2.37-2.45 (m, 4H), 3.60-3.72 (m, 2H), 4.05 (s, 3H), 4.06-4.18 (m, 4H), 4.44 (d, 1H, J=15 Hz), 5.33 (d, 1H, J=14 Hz), 5.49 (s, 1H), 6.17 (br s, 1H), 6.98-7.08 (m, 2H), 7.33-7.43 (m, 2H), 7.55-7.63 (m, 1H), 8.50-8.57 (br d, 1H), 8.97 (br s, 1H); 31P (121.4 MHz, CDCl3) δ 22.7; 19F NMR (282.6 MHz, CDCl3) δ 62.6; EI MS (m/z) 590.4 [M−H]−, 614.2 [M+Na].

Aufarbeitung

  1. additionwere added

Quellen und Nachweise

ORD-Eintrag
ord-3f236d19e45146df80ee5ca44c04116c
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253180B2

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