4-Toluenesulfonyl chloride → [3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonate

HRID 15138

Reaktionsgleichung

Reaktionsgleichung von HRID 15138
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[C:7]([F:18])[C:8](=[O:17])[N:9]3[CH2:13][C:12]([OH:16])([CH2:14][OH:15])[C:11]=1[C:10]=23.C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl.O1CCCC1.C([Sn](=O)CCCC)CCC>[CH3:36][C:26]1[CH:31]=[CH:30][C:29]([S:32]([O:15][CH2:14][C:12]2([OH:16])[C:11]3=[C:2]([F:1])[CH:3]=[N:4][C:5]4[CH:6]=[C:7]([F:18])[C:8](=[O:17])[N:9]([C:10]=43)[CH2:13]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Komponenten

7

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 236342743,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Produkt 1

HCID 86614148[3,8-difluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl]methyl 4-methylbenzenesulfonateAusbeute 105,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 61221Dibutyltin oxideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3,8-difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (710 mg, 2.79 mmol) in dichloromethane (35 ml) and tetrahydrofuran (35 ml) was treated with triethylamine (0.58 ml, 4.19 mmol), para-toluenesulphonyl chloride (586 mg, 3.07 mmol) and dibutyltin oxide (35 mg, 0.14 mmol). After 6 hours stirring at room temperature under argon, the mixture was evaporated and water (200 ml) was added. The aqueous phase was extracted with dichloromethane (3×200 ml) and the combined organic extracts dried over magnesium sulphate and evaporated to give the desired compound (1.2 g, 100%) which was used without further purification.

Aufarbeitung

  1. customthe mixture was evaporated
  2. additionwater (200 ml) was added
  3. extractionThe aqueous phase was extracted with dichloromethane (3×200 ml)
  4. dry with materialthe combined organic extracts dried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-498ff0b85cae4603b807ffefd9dc6953
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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