Diisopropylethylamine → HCID 22258319, Verbindung

HRID 2244127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244127
Cl.[CH2:2]([C@@H:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][CH2:11][C@@H:10]1[NH2:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[N:31]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=1)=[C:32]=[S:33]>C(#N)C>[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[NH:21][C:32]([NH:31][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=1)=[S:33])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 20637794cis-1-Benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochlorideHCID 22258323HCID 22258323, Verbindung

Produkt 1

HCID 22258319HCID 22258319, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of cis-1-benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride (0.306 g, 1.01 mmol), diisopropylethylamine (0.264 mL, 1.51 mmol) and 4-isothiocyanatomethyl-2-methoxy-1-methoxymethoxy-benzene (0.253 g, 1.06 mmol) in acetonitrile (10 mL) was stirred at ambient temperature overnight. The solvent was evaporated in vacuo, and the residue was purified by reverse phase preparative HPLC, on a C18 column eluted with a gradient of 40 to 90% acetonitrile in water with 0.1% TFA, to give the product, 1-(1-benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(3-methoxy-4-methoxymethoxy-benzyl)-thiourea, 0.21 g (41%). 1H NMR (CDCl3): δ 1.64 (br s, 1H), 1.85 (m, 1H), 2.04 (m, 1H), 2.63 (m, 1H), 2.82 (m, 2H), 2.98 (m, 1H), 3.33 (m, 1H), 3.49 (s, 3H), 3.78 (s, 3H), 3.84 (s, 3H), 4.32 (br s, 2H), 5.19 (s, 2H), 5.7 (br s, 1H), 6.0 (br s, 1H), 6.64 (m, 3H), 6.80 (s, 1H), 6.91 (d, J=8.4 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H) and 7.11 to 7.28 (m, 5H). MS: m/z 507 (M+H)+.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by reverse phase preparative HPLC, on a C18 column
  3. washeluted with a gradient of 40 to 90% acetonitrile in water with 0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-7acb728466fa46b493ba5604cef37536
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678812B2

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