Methyl iodide → HCID 70872663, Verbindung

HRID 73012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73012
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:18][CH2:17][C:16]3([CH2:23][NH:22][CH2:21][CH:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:19]3)[CH2:15][CH2:14]2)=[O:12])=[CH:7][C:6]=1[CH3:30])([CH3:3])[CH3:2].IC.[CH2:33](N(CC)CC)C.C(Cl)[Cl:41]>>[ClH:41].[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:14][CH2:15][C:16]3([CH2:23][N:22]([CH3:33])[CH2:21][CH:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:19]3)[CH2:17][CH2:18]2)=[O:12])=[CH:7][C:6]=1[CH3:30])([CH3:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 68291585HCID 68291585, Verbindung

Produkt 1

HCID 70872663HCID 70872663, VerbindungAusbeute 54 %

Versuchsvorschrift

To (4-isopropoxy-3-methyl-phenyl)-(8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)methanone (22 mg, 0.05 mmol) in DCM (0.3 mL) was added iodomethane (15 mg, 7 μL, 0.11 mmol) followed by the addition of triethylamine (15 μL, 0.11 mmol) and the reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated in vacuo, diluted with methanol, filtered and purified by prep LCMS (1-99% ACN/H2O, 5 mM HCl modifier) to give (4-isopropoxy-3-methyl-phenyl)-(10-methyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)methanone hydrochloride salt as a glassy solid (13 mg, 54%). ESI-MS m/z calc. 422.3. Found 423.5 (M+1)+; Retention time: 1.31 minutes (3 min run).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with methanol
  3. filtrationfiltered
  4. custompurified by prep LCMS (1-99% ACN/H2O, 5 mM HCl modifier)

Quellen und Nachweise

ORD-Eintrag
ord-4e302590f12e4ad2b224e3c2ee5e8f1c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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