Sodium borohydride → 2-[4-[5-[(1,5-Dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-10-fluoro-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one

HRID 593014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593014
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:35][CH2:34][C:33]5[N:32]6[C:27]([CH2:28][CH2:29][CH2:30][CH2:31]6)=[C:26]([F:36])[C:25]=5[C:24]4=[O:37])[C:18]=3[CH:38]=[O:39])[CH:10]=2)=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:35][CH2:34][C:33]5[N:32]6[C:27]([CH2:28][CH2:29][CH2:30][CH2:31]6)=[C:26]([F:36])[C:25]=5[C:24]4=[O:37])[C:18]=3[CH2:38][OH:39])[CH:10]=2)=[N:3]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866844934-{5-[(1,5-Dimethyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydro pyridin-3-yl}-2-{10-fluoro-1-oxo-1H,2H,3H,4H,6H,7H,8H,9H-pyrido[3,4-b]indolizin-2-yl}pyridine-3-carbaldehyde

Produkt 1

HCID 866844942-[4-[5-[(1,5-Dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-10-fluoro-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 261a (90.0 mg, 0.17 mmol) in methanol (5 mL) was added sodium borohydride (64.6 mg, 1.7 mmol) at room temperature. The reaction was stirred for 0.5 h. It was then quenched with water (2 mL) and evaporated in vacuo. The residue was extracted with dichloromethane (3×10 mL). The combined dichloromethane extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 261 (47.0 mg, 52%) as a white solid. MS-ESI: [M+H]+ 532.3. 1H NMR (500 MHz, DMSO-d6) δ 8.47 (d, J=5.0 Hz, 1H), 8.05 (s, 1H), 8.03 (d, J=2.5 Hz, 1H), 7.39 (d, J=2.5 Hz, 1H), 7.31 (d, J=5.0 Hz, 1H), 5.89 (s, 1H), 4.87-4.85 (m, 1H), 4.45-4.36 (m, 2H), 4.11-4.09 (m, 1H), 3.93-3.91 (m, 1H), 3.79-3.76 (m, 2H), 3.59 (s, 3H), 3.58 (s, 3H), 3.00-2.94 (m, 2H), 2.66-2.63 (m, 2H), 2.18 (s, 3H), 1.90-1.88 (m, 2H), 1.78-1.73 (m, 2H)

Aufarbeitung

  1. customIt was then quenched with water (2 mL)
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with dichloromethane (3×10 mL)
  4. extractionThe combined dichloromethane extract
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by reverse-phase prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-03daec67bbea441eac6535f69df01ebc
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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