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

HRID 1394188ノート

反応式

HRID 1394188 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4c4e98340523408bb18625e72a0fd424
出典データセット
uspto-grants-2008_03
特許番号
US07348339B2

反応ノート

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