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

HRID 450598

반응식

HRID 450598 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-bfefea6160f34386aa322fc6dbb57206
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486979B2

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