Sodium borohydride → 2-[4-[5-[(5-ethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one

HRID 1411818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1411818
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH:12][C:13]3[C:18](=[O:19])[N:17]([CH3:20])[CH:16]=[C:15]([C:21]4[C:26]([CH:27]=[O:28])=[C:25]([N:29]5[CH2:41][CH2:40][C:39]6[N:38]7[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]7)=[CH:32][C:31]=6[C:30]5=[O:42])[N:24]=[CH:23][CH:22]=4)[CH:14]=3)[CH:11]=[C:5]2[CH2:4]1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH:12][C:13]3[C:18](=[O:19])[N:17]([CH3:20])[CH:16]=[C:15]([C:21]4[CH:22]=[CH:23][N:24]=[C:25]([N:29]5[CH2:41][CH2:40][C:39]6[N:38]7[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]7)=[CH:32][C:31]=6[C:30]5=[O:42])[C:26]=4[CH2:27][OH:28])[CH:14]=3)[CH:11]=[C:5]2[CH2:4]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866843894-(5-(5-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydro-pyrido[3,4-b]indolizin-2(1H)-yl)nicotinaldehyde

Produkt 1

HCID 715579162-[4-[5-[(5-ethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-oneAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 208e (95 mg, 0.16 mmol) at 0° C. in methanol (10 mL) was added sodium borohydride (19 mg, 0.50 mmol). The reaction mixture was stirred for 30 minutes and quenched with water (2.0 mL). It was then concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 208 (8 mg, 9%) as white solid. MS-ESI: [M+H]+ 569.3. 1H NMR (500 MHz, CDCl3) δ 8.46 (d, J=5.0 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H, 7.70 (d, J=2.0 Hz, 1H), 7.40 (s, 1H), 7.30 (d, J=5.0 Hz, 1H), 6.30 (s, 1H), 5.71 (s, 1H), 4.93-4.96 (m, 1H), 4.63-4.61 (m, 1H), 4.42-4.26 (m, 2H), 4.09 (s, 2H), 3.94-3.81 (m, 3H), 3.69-3.68 (m, overlap, 5H), 3.06-2.90 (m, 4H), 2.81 (d, J=3.0 Hz, 2H), 2.66 (d, J=3.5 Hz, 2H), 2.04-2.00 (m, 2H), 1.88-1.85 (m, 2H), 1.20 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. customquenched with water (2.0 mL)
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e36d78cdc9994a53befc14de233a12ad
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921353B2

Notizen zur Reaktion

Wird geladen…