4-Hydrazinyl-1-methylpiperidine → 2-(5-(9-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-2-yl)-1H-1,2,4-triazol-1-yl)ethanol

HRID 1530654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530654
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[C:17]1[N:13]([CH:14]=[C:15]([C:21]3[N:25]([CH2:26][CH2:27][OH:28])[N:24]=[CH:23][N:22]=3)[N:16]=1)[CH2:12][CH2:11][O:10]2)=O.[NH:30]([CH:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1)[NH2:31]>C(O)(=O)C>[CH3:38][N:35]1[CH2:36][CH2:37][CH:32]([N:30]2[C:5]([C:7]3[CH:20]=[CH:19][C:18]4[C:17]5[N:13]([CH:14]=[C:15]([C:21]6[N:25]([CH2:26][CH2:27][OH:28])[N:24]=[CH:23][N:22]=6)[N:16]=5)[CH2:12][CH2:11][O:10][C:9]=4[CH:8]=3)=[CH:4][CH:3]=[N:31]2)[CH2:33][CH2:34]1

Komponenten

4

Edukt 2

HCID 109205354-Hydrazinyl-1-methylpiperidineHCID 68312848(2E)-3-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-one

Produkt 1

HCID 665589232-(5-(9-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-2-yl)-1H-1,2,4-triazol-1-yl)ethanolAusbeute 13,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of (2E)-3-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-one (105 mg, 0.270 mmol) in acetic acid (2.0 mL) was added hydrochloric 4-hydrazinyl-1-methylpiperidine (53 mg, 0.32 mmol). The mixture was stirred at 100° C. for 1 hour under nitrogen atmosphere. After concentration, the residue was purified by preparative HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give 257 (17 mg, 13% yield). LCMS (ESI): RT=4.05 min, m/z: 461.2 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.55 (d, J=8.5 Hz, 1H), 8.10 (s, 1H), 7.94 (s, 1H), 7.55 (d, J=1.5 Hz, 1H), 7.23 (d, J=9 Hz, 1H), 7.11 (s, 1H), 6.40 (d, J=1.5 Hz, 1H), 4.98 (t, J=10.5, 1H), 4.84 (t, J=12, 2H), 4.58 (s, 4H), 4.16 (t, J=23 Hz, 1H), 3.88-3.86 (m, 2H), 2.85 (d, J=10 Hz, 2H), 2.15-2.13 (m, 5H), 1.94 (s, 2H), 1.81 (d, J=11.5, 2H)

Aufarbeitung

  1. concentrationAfter concentration
  2. customthe residue was purified by preparative HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Quellen und Nachweise

ORD-Eintrag
ord-8c1d09967d424340a3e9d8341c4444c5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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