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Methyl iodide → 5'-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2'-(isopropoxymethyl)-N,N-dimethylbiphenyl-4-carboxamide

HRID 640633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 640633
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3([C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([CH3:35])=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:26][CH:25]=5)[CH:23]=4)=[O:16])[CH2:14][CH2:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1.IC>O1CCCC1.CN(C)C=O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3([C:15]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([CH2:35][O:3][CH:7]([CH3:8])[CH3:6])=[C:22]([C:24]5[CH:25]=[CH:26][C:27]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:28][CH:29]=5)[CH:23]=4)=[O:16])[CH2:14][CH2:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1
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Komponenten

6

Edukt 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 592065844-[5-(1-benzo[1,3]dioxol-5-ylcyclopropyl)carbonylamino-2-methyl-phenyl]-N,N-dimethyl-benzamide

Produkt 1

HCID 592066525'-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2'-(isopropoxymethyl)-N,N-dimethylbiphenyl-4-carboxamideAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (2.2 mg, 0.055 mmol, 60% by weight dispersion in oil) was slowly added to a stirred solution of 5′-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-N,N,2′-trimethylbiphenyl-4-carboxamide (21 mg, 0.048 mmol) in a mixture of 0.90 mL of anhydrous tetrahydrofuran (THF) and 0.10 mL of anhydrous N,N-dimethylformamide (DMF). The resulting suspension was allowed to stir for 3 minutes before iodomethane (0.0048 mL, 0.072 mmol) was added to the reaction mixture. An additional aliquot of sodium hydride and iodomethane were required to consume all of the starting material which was monitored by LCMS. The crude reaction product was evaporated to dryness, redissolved in a minimum of DMF and purified by preparative LCMS chromatography to yield 5′-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2′-(isopropoxymethyl)-N,N-dimethylbiphenyl-4-carboxamide (9.1 mg, 42%) ESI-MS m/z calc. 456.2, found 457.5 (M+1)+. Retention time of 2.94 minutes. 1H NMR (400 MHz, CD3CN) δ 0.91-0.93 (m, 2H), 1.41-1.45 (m, 2H), 2.23 (s, 3H), 3.00 (s, 3H), 3.07 (s, 3H), 3.20 (s, 3H), 5.81 (s, 2H), 6.29-6.36 (m, 2H), 6.56 (d, J=8.0 Hz, 1H), 6.69 (s, 1H), 6.92 (dd, J=1.6, 7.9 Hz, 1H), 7.17 (d, J=8.1 Hz, 1H), 7.28 (d, J=8.1 Hz, 2H), 7.46 (dd, J=1.8, 6.4 Hz, 2H).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customto consume all of the starting material which
  3. customThe crude reaction product
  4. customwas evaporated to dryness
  5. dissolutionredissolved in a minimum of DMF
  6. custompurified by preparative LCMS chromatography

Quellen und Nachweise

ORD-Eintrag
ord-300c6371491f4712b4d0da3ac4f7b2c6
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691902B2

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