1-Hydroxybenzotriazole → 5-(5-(Pyrrol-1-yl)pyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 450598

Reaction equation

HRID 450598 reaction equation
[N:1]1([C:6]2[CH:7]=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl.CNCCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O[N:37]=[C:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=1>CN(C)C=O>[N:1]1([C:6]2[CH:14]=[C:10]([C:11]3[O:13][N:45]=[C:38]([C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)[N:37]=3)[CH:9]=[N:8][CH:7]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 308113N-HydroxynicotinimidamideHCID 20501015-(1H-pyrrol-1-yl)pyridine-3-carboxylic acidHCID 9794023N-(3-methylaminopropyl)-N'-ethylcarbodiimide hydrochloride

Product 1

HCID 670265495-(5-(Pyrrol-1-yl)pyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1H-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. N′-Hydroxynicotinimidamide (137 mg, 1.0 mmol) was added and the mixture was stirred for 6-10 hours, and then warmed to 140° C. 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. 1H 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, 1H), 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=1.7 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)+.

Workup

  1. stirringthe mixture was stirred for 6-10 hours
  2. temperaturewarmed to 140° C. for 2-4 hours
  3. temperatureThe reaction was cooled to ambient temperature
  4. customtriturated with water (10 mL)
  5. filtrationThe precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bfefea6160f34386aa322fc6dbb57206
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Linked notes

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