Sodium borohydride → 6-tert-butyl-2-[4-[5-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-one

HRID 407715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407715
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:40]=[C:35]5[CH2:36][O:37][CH2:38][CH2:39][N:34]5[N:33]=4)[C:28](=[O:41])[N:27]([CH3:42])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:40]=[C:35]5[CH2:36][O:37][CH2:38][CH2:39][N:34]5[N:33]=4)[C:28](=[O:41])[N:27]([CH3:42])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866839832-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(5-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde

Produkt 1

HCID 866839846-tert-butyl-2-[4-[5-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-8-fluoro-phthalazin-1-oneAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 131e (220 mg, 1.0 eq., 0.39 mmol), NaBH4 (73 mg, 5.0 eq., 1.90 mmol), and methanol (10 mL). The mixture was stirred at room temperature for 1 h and quenched with water (5 mL). It was then concentrated under reduced pressure and resulting residue was extracted with dichloromethane (3×10 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 131 (105 mg, 47%). MS-ESI: [M+H]+ 571.8. 1H NMR (500 MHz, CDCl3) δ 8.66 (d, J=5.0 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H), 8.03 (d, J=2.5 Hz, 1H), 7.59-7.53 (m, 4H), 7.48 (s, 1H), 5.73 (s, 1H), 4.81 (s, 2H), 4.51 (bs, 2H), 4.12-4.05 (m, overlap, 5H), 3.73 (s, 3H), 1.46 (s, 9H).

Aufarbeitung

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customquenched with water (5 mL)
  3. concentrationIt was then concentrated under reduced pressure
  4. customresulting residue
  5. extractionwas extracted with dichloromethane (3×10 mL)
  6. concentrationThe combined organic layer was concentrated under reduced pressure
  7. customthe residue was purified by reverse-phase prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dbd51347e6f74d7283c0f642ab930106
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754077B2

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