Methyl iodide → HCID 70872663, Verbindung

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Reaktionsgleichung

[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

Edukt 4

HCID 6328Methyl iodide

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 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

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

Quellen und Nachweise

ORD-Eintrag: ord-0b79a0abc8d2408cbc26b8b43f16291e
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09181273B2

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