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690632-31-6

5-(1H-PYRROL-1-YL)NICOTINIC ACID synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: 5-(1H-pyrrol-1-yl)nicotinic acidwith benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide at 20; for 0.333333 h;
Stage #2: N-hydroxy-3-pyridinecarboximidamide in N,N-dimethyl-formamide at 20 - 140; for 8 - 14 h;

Steps:

8

To a solution of 5-(1 H-pyrrol-1 -yl)nicotinic acid (Maybridge, 188 mg, 1 .00 mmol) in dimethylformamide (anhydrous, 5 mL) was added N-(3- methylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) (Aldrich, 192 mg, 1 .00 mmol) and 1 -hydroxybenzotriazole (HOBT) hydrate (Fluka, 153 mg, 1 .00 mmol). The mixture was stirred at ambient temperature for 20 minutes. λ/'-Hydroxynicotinimidamide (137 mg, 1 .0 mmol) was added and the mixture was stirred for 6-10 hours, and then warmed to 140 0C for 2-4 hours. The reaction was cooled to ambient temperature and triturated with water (10 ml_). The precipitate was filtered and dried under vacuum to give the titled compound. 1 H NMR (300 MHz, DMSO-d6) δ 6.34 - 6.44 (m, 2 H), 7.60 - 7.82 (m, 3 H), 8.50 (dt, J=8.1 , 1 .9 Hz, 1 H), 8.71 (dd, J=2.5, 1 .9 Hz, 1 H), 8.84 (dd, J=4.6, 1 .5 Hz, 1 H), 9.21 (d, J=M Hz, 1 H), 9.26 (d, J=2.4 Hz, 1 H), 9.31 (d, J=1 .7 Hz, 1 H) ppm; MS (DCI/NH3) m/z 290 (M+H)+.

References:

WO2008/73942,2008,A2 Location in patent:Page/Page column 39; 40

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