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Water → 3-(Phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047123
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1047123
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[N:15][C:16]([NH:28][C:29](=[O:33])[NH:30][CH2:31][CH3:32])=[CH:17][C:18]=3[C:19]3[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=3)=[CH:10][N:11]=2)[C:6](=[O:34])[C:5]([C:35]([O:37][CH2:38][CH2:39][CH2:40][O:41][P:42]([O:52]CC2C=CC=CC=2)([O:44]CC2C=CC=CC=2)=[O:43])=[O:36])=[CH:4]1)[CH3:2].C[Si](Br)(C)C.O>ClCCl.CO>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[N:15][C:16]([NH:28][C:29](=[O:33])[NH:30][CH2:31][CH3:32])=[CH:17][C:18]=3[C:19]3[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=3)=[CH:10][N:11]=2)[C:6](=[O:34])[C:5]([C:35]([O:37][CH2:38][CH2:39][CH2:40][O:41][P:42]([OH:44])([OH:52])=[O:43])=[O:36])=[CH:4]1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 687463213-{[Bis(benzyloxy)phosphoryl]oxy}propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 687478433-(Phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Ausbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-{[Bis(benzyloxy)phosphoryl]oxy}propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 21, 700 mg, 0.82 mM) was dissolved in dry dichloromethane (40 mL), and the reaction mixture was cooled to 0° C. Trimethylsilyl bromide (251 mg, 1.64 mmol) was added and the mixture was stirred for 16 h at room temperature. A solid formed on the walls of round bottom flask. The solvent was decanted and the solid was washed with ethyl acetate (30 mL) to give crude compound. The crude compound was dissolved in methanol (20 mL) and water (30 mL) was added to precipitate the product which was filtered and dried to afford 230 mg (35%) of 3-(phosphonooxy)propyl 1-ethyl-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate.

Aufarbeitung

  1. customA solid formed on the walls of round bottom flask
  2. customThe solvent was decanted
  3. washthe solid was washed with ethyl acetate (30 mL)
  4. customto give crude compound
  5. customto precipitate the product which
  6. filtrationwas filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5973762b95c949fb848785701b03830b
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569484B2

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