Bromine → 4-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

HRID 1394188노트

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HRID 1394188 반응식
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:17])=[N:14][O:15][N:16]=1)[CH3:2].[Br:18]Br>C(O)(=O)C>[Br:18][C:10]1[C:11]2[N:3]([CH2:1][CH3:2])[C:4]([C:12]3[C:13]([NH2:17])=[N:14][O:15][N:16]=3)=[N:5][C:6]=2[CH:7]=[N:8][CH:9]=1

참가 물질

4

반응물 2

HCID 24408BromineHCID 236465784-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

생성물 1

HCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine수율 43%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a solution of the product of Example 1 Step 1 (3.0 g, 17.9 mmol) in acetic acid (40 ml) was added bromine (3.12 g, 1 ml, 19.7 mmol) and the mixture was heated at 100° C. for 20 hours. After cooling the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was washed with water (×3), dried and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 50% dichloromethane in ethyl acetate afforded the title compound (1.9 g, 43%). 1H NMR (DMSO-d6) 8.73 (1H, s), 8.52 (1H, s), 7.0 (1H, br), 3.25 (2H, m), 1.16 (3H, t, J=7.2 Hz).

후처리

  1. temperatureAfter cooling the solvent
  2. customwas removed in vacuo
  3. customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
  4. washThe organic phase was washed with water (×3)
  5. customdried
  6. customevaporated in vacuo
  7. customPurification of the residue by silica gel chromatography
  8. washeluting with 50% dichloromethane in ethyl acetate

출처 및 근거

ORD 기록
ord-4c4e98340523408bb18625e72a0fd424
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348339B2

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