Triethylamine → HCID 178492638, Verbindung

HRID 1096883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096883
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)[C:25](O)=[O:26])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl.[NH:34]1[C:38]([C:39]2[CH:40]=[C:41]3[C:51](=[CH:52][CH:53]=2)[O:50][C:44]2([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:43][C:42]3=[O:54])=[N:37][N:36]=[N:35]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN1C(=O)CCC1.C(Cl)(Cl)Cl>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([C:25]([N:47]4[CH2:48][CH2:49][C:44]5([CH2:43][C:42](=[O:54])[C:41]6[C:51](=[CH:52][CH:53]=[C:39]([C:38]7[NH:37][N:36]=[N:35][N:34]=7)[CH:40]=6)[O:50]5)[CH2:45][CH2:46]4)=[O:26])[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579309723-(1H-indol-5-yl)-5-methoxybenzoic acidHCID 178479612HCID 178479612, Verbindung

Produkt 1

HCID 178492638HCID 178492638, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

WSC hydrochloride (52.5 mg, 0.274 mmol) was added to a mixture of 3-(1H-indol-5-yl)-5-methoxybenzoic acid (61.0 mg, 0.228 mmol), 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (73.4 mg, 0.228 mmol), HOBT (34.9 mg, 0.228 mmol), triethylamine (0.048 mL, 0.34 mmol), chloroform (0.4 mL) and NMP (0.8 mL), and stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile) to obtain the title compound as a pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 11.18 (1H, s), 8.43 (1H, d J=2.3 Hz), 8.25 (1H, dd, J=8.8, 2.3 Hz), 7.87-7.86 (1H, m), 7.47 (1H, d, J=8.4 Hz), 7.41 (1H, dd, J=8.4, 1.7 Hz), 7.39 (1H, t, J=2.8 Hz), 7.35 (1H, d, J=8.8 Hz), 7.26 (1H, dd, J=2.4, 1.5 Hz), 7.24 (1H, t, J=1.5 Hz), 6.87 (1H, dd, J=2.4, 1.5 Hz), 6.49 (1H, ddd, J=2.8, 2.1, 0.7 Hz), 4.37-4.23 (1H, m), 3.86 (3H, s), 3.66-3.18 (3H, m), 2.99 (2.0H, s), 2.14-1.81 (4H, m). MS [M−H]−=533.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified through high-performance preparative liquid chromatography (0.1% TFA, water/acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-e64a538db44a4592ad23ae6921598aa2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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