Sodium borohydride → 6-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-One

HRID 407644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407644
[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:37]=[CH:36][N:35]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[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:37]=[CH:36][N:35]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[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 866839322-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)nicotinaldehyde

Produkt 1

HCID 866839336-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-OneAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 113c (80 mg, 0.14 mmol), NaBH4 (27 mg, 0.70 mmol), and methanol (10 mL) was stirred at room temperature for 0.5 h. The mixture was quenched with water (2 mL) and concentrated under reduced pressure. The residue was purified with reverse-phase prep-HPLC to afford 113 (57 mg, 71%). MS-ESI: [M+H]+ 528.3. 1H NMR (500 MHz, DMSO-d6) δ 9.26 (s, 1H), 8.76 (d, J=2.5 Hz, 1H), 8.67 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 8.54 (d, J=2.5 Hz, 1H), 8.31 (d, J=6.0 Hz, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.79-7.76 (m, 1H), 7.69 (d, J=2.0 Hz 1H), 7.54 (d, J=5.0, Hz 1H), 7.34-7.32 (m, 1H), 4.94 (t, J=5.0 Hz, 1H), 4.42-4.40 (m, 2H), 3.62 (s, 3H), 1.39 (s, 9H).

Aufarbeitung

  1. customThe mixture was quenched with water (2 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with reverse-phase prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5a25a8dab3414e68a4bbcbc078c84b64
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754077B2

Notizen zur Reaktion

Wird geladen…