Triethylamine → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

HRID 452262

Reaktionsgleichung

Reaktionsgleichung von HRID 452262
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[C:19]2[CH2:26][C:27]([OH:29])=O.CCN=C=NCCCN(C)C.[ClH:41].[CH:42]1[CH:43]=[CH:44][C:45]2N(O)N=N[C:46]=2[CH:47]=1.C(N(CC)CC)C>ClCCl>[Cl:41][C:42]1[CH:47]=[C:46]2[C:45](=[CH:44][CH:43]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:27](=[O:29])[CH2:26][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=2)[NH:21][C:20]=1[CH3:25]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Produkt 1

HCID 44132757N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (195 mg, 0.896 mmol) in presence of EDCI.HCl (256 mg, 1.345 mmol), HOBt (205 mg, 1.345 mmol) and triethylamine (374 μl, 3.003 mmol) in dichloromethane (10 ml) as described in Example 1 to give 35 mg of the product as a white solid; IR (KBr) 3383, 2934, 2343, 1648, 1475, 1217, 820 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.50-1.65 (m, 5H), 1.83-1.95 (m, 3H), 2.40 (s, 3H), 3.73 (s, 3H), 3.82 (s, 2H), 5.23 (q, J=9.6 Hz, 1H), 5.76 (d, J=8.7 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.77 (dd, J=2.4, 6.6 Hz, 1H), 6.82-6.89 (m, 2H), 6.98 (dd, J=2.1, 6.3 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.84 (s, 1H); ESI-MS (m/z) 423.58 (M−H)−.

Quellen und Nachweise

ORD-Eintrag
ord-d5baacfe4c6e4c708efa07ca1ad92164
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487121B2

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