Tryptamine → 3-[(2S*,5R*)-5-{[2-(1H-Indol-3-yl)-ethylcarbamoyl]-methyl}-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-3-yl]-propionamide

HRID 2230806

Reaktionsgleichung

Reaktionsgleichung von HRID 2230806
[C:1]([CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH2:12][C:13](O)=[O:14])[S:8][CH:7]1[C:16]1[S:17][C:18]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:20]=1)(=[O:3])[NH2:2].[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][CH2:39][NH2:40])=[CH:30]1.C(P(=O)(OCC)OCC)#N.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][CH2:39][NH:40][C:13]([CH2:12][C@H:9]2[S:8][C@@H:7]([C:16]3[S:17][C:18]([C:21]#[C:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:20]=3)[N:6]([CH2:5][CH2:4][C:1]([NH2:2])=[O:3])[C:10]2=[O:11])=[O:14])=[CH:30]1

Komponenten

7

Edukt 4

HCID 1150TryptamineHCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 86758382[3-(2-Carbamoyl-ethyl)-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-5-yl]-acetic acid

Produkt 1

HCID 867583833-[(2S*,5R*)-5-{[2-(1H-Indol-3-yl)-ethylcarbamoyl]-methyl}-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-3-yl]-propionamideAusbeute 16,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of [3-(2-carbamoyl-ethyl)-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-5-yl]-acetic acid (1.36 g,3.28 mmol), 3-indolylethylamine (0.77 g, 4.8 mmol), diethyl cyanophosphonate (0.781 g, 4.8 mmol) and diisopropylethylamine (0.62 g, 4.8 mmol) was stirred in DMF (50 mL) for three hours at room temperature. The mixture was poured into water (100 mL). The product was extracted into ethyl acetate (2×100 mL). The extract was washed successively with sat. NaHCO3, H2O, brine, and then dried (MgSO4). The solvent was evaporated to a brown gum, which was washed twice with methanol to remove the dark color to provide the title compound as an off-white solid (0.3 g, 16.8%). 1H NMR (DMSO-d6) δ 10.8 (s, 1H), 8.19-8.23 (t, 1H), 7.51-7.55 (m, 3H), 7.33-7.46 (m, 4H), 7.27-7.31 (m, 3H), 7.14-7.15 (d, 1H, J=2.2 Hz), 7.02-7.07 (t, 1H), 6.91-6.98 (m, 2H), 6.13 (s, 1H ), 4.15-4.20 (dd, 1H, J=3.1 Hz ), 3.55-3.64 (m, 1H), 3.27-3.41 (m, 2H), 2.97-3.07 (m, 2H), 2.79-2.84 (t, 2H), 2.60 (s, 1H), 2.55-2.56 (d, 1H, J=4.7 Hz), 2.35-2.45 (m,1H), 2.08-2.18 (m, 1H), 95% cis based on peaks at δ 6.13 and 4.15-4.20); MS(ESI)557[M+H]+.FTIR(ATR) 1620, 1660 cm−1.Anal.(C30H28N4O3S2) calc. C, 64.72; H, 5.07; N, 10.06. Obs. C, 64.55; H, 4.98; N, 9.93.

Aufarbeitung

  1. extractionThe product was extracted into ethyl acetate (2×100 mL)
  2. washThe extract was washed successively with sat. NaHCO3, H2O, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated to a brown gum, which
  5. washwas washed twice with methanol
  6. customto remove the dark color

Quellen und Nachweise

ORD-Eintrag
ord-580f3370a3e74d03a61357e74fca06ee
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06426357B1

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