3-Methoxypropylamine → N-(3-methoxypropyl)-2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxamide

HRID 42315

Reaktionsgleichung

Reaktionsgleichung von HRID 42315
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[S:14][CH:15]=[C:16]([C:18]([OH:20])=O)[N:17]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:42][O:43][CH2:44][CH2:45][CH2:46][NH2:47].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:42][O:43][CH2:44][CH2:45][CH2:46][NH:47][C:18]([C:16]1[N:17]=[C:13]([C:10]2[CH:11]=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][CH:9]=2)[S:14][CH:15]=1)=[O:20]

Komponenten

7

Edukt 5

HCID 16723-MethoxypropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 592524752-(2-Phenylpyrimidin-5-yl)thiazole-4-carboxylic acid

Produkt 1

HCID 59252401N-(3-methoxypropyl)-2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution consisting of 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylic acid (Example 63, 80 mg, 0.28 mmol) in dichloromethane (10 mL) was added EDAC (75 mg, 0.39 mmol) and HOBt (53 mg, 0.39 mmol) at 0° C. To this mixture was added 3-methoxypropylamine (25 mg, 0.28 mmol) dissolved in dichloromethane (2 mL) and diisopropylethylamine (0.52 mL, 390 mg, 3.0 mmol). The solution was allowed to reach room temperature and stirred for 18 hours. The solvent was evaporated away under reduced pressure and the residue was purified by silica gel flash chromatography (1:1 v/v hexane-ethyl acetate to 100% ethyl acetate gradient) through a 25-g Silicycle® flash silica cartridge. The title compound was obtained as an off-white solid (21 mg, 21% yield); Rf 0.70 with 4:1 v/v ethyl acetate-hexane; melting point 134-136° C.; 1H-NMR (300 MHz; CDCl3) δ 9.31 (s, 2H), 8.52 (dd, 2H), 8.20 (s, 1H), 7.88 (br t, 1H), 7.53 (m, 3H), 3.62 (t, 2H); 3.59 (t, 2H); 3.41 (s, 3H), 1.96 (m, 2H); MS (ESI+) m/z 355 (M+1); H-PGDS FPBA IC50: 3.4 μM.

Aufarbeitung

  1. customto reach room temperature
  2. customThe solvent was evaporated away under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography (1:1 v/v hexane-ethyl acetate to 100% ethyl acetate gradient) through a 25-g Silicycle® flash silica cartridge

Quellen und Nachweise

ORD-Eintrag
ord-ad6c6539b9aa414784569152efc8236a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536185B2

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