Bromine → HCID 178508259、化合物

HRID 1452764ノート

反応式

HRID 1452764 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[S:15])[NH:11][N:12]=1.BrBr>CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[S:15][C:14]([NH2:16])=[N:13][C:10]=2[NH:11][N:12]=1

参加物

4

反応物 2

HCID 24408BromineHCID 178514156HCID 178514156、化合物

生成物 1

HCID 178508259HCID 178508259、化合物収率 37%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To a solution of [5-(2-bromo-phenyl)-2H-pyrazol-3-yl]-thiourea (1.6 g, 5.38 mmol) in glacial AcOH (200 mL) was added a 1.5 M solution of bromine in AcOH (3.59 mL, 5.38 mmol) dropwise under vigorous stirring. The resulting heterogeneous mixture was stirred at room temperature for 2 hours then at 80° C. for 1 hour. The reaction was cooled to room temperature and concentrated to dryness. Water was added followed by 1 N aqueous NaOH to neutralize to pH 7. The resulting precipitate was filtered, washed with water and dried in vacuo. The solid was then refluxed in MeOH for 2 hours, filtered and washed with MeOH to give 588 mg of pure 3-(2-bromo-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine as an off-white solid. The filtrate was further purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide another 460 mg of 3-(2-bromo-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine for a total of 1.408 g (88% yield). 1H-NMR (d6-DMSO) δ: 13.1 and 12.6 (2 broad s, 1H, NH+tautomer), 7.73 (d, 1H), 7.61 (broad m, 1H), 7.48 (m, 3H), 7.34 (t, 1H); HPLC/MS m/z: 294.9, 296.9 [MH]+.

後処理

  1. waitat 80° C. for 1 hour
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated to dryness
  4. additionWater was added
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo
  8. temperatureThe solid was then refluxed in MeOH for 2 hours
  9. filtrationfiltered
  10. washwashed with MeOH

出典と根拠

ORDレコード
ord-3039d919dd97459f9240a09335bcbc0d
出典データセット
uspto-grants-2009_01
特許番号
US07473783B2

反応ノート

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