Cyanogen Bromide → 5,6-difluoro-1H-1,3-benzodiazol-2-amine

HRID 30895

反応式

HRID 30895 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH2:10].[N:11]#[C:12]Br.C(=O)(O)[O-].[Na+]>O>[F:8][C:6]1[C:5]([F:9])=[CH:4][C:3]2[NH:10][C:12]([NH2:11])=[N:1][C:2]=2[CH:7]=1

参加物

5

反応物 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 27367551,2-Diamino-4,5-difluorobenzene

生成物 1

HCID 106787085,6-difluoro-1H-1,3-benzodiazol-2-amine収率 98.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Step 1 The procedure used was similar to that reported in J. Med. Chem. 40:811-818, 1997. A solution of 1,2-diamino-4,5-difluorobenzene (500 mg, 3.47 mmol) in water (5 mL) was cooled to 0° C. and then treated with a solution of cyanogen bromide (0.83 mL, 4.16 mmol, 5 M in acetonitrile) and solid sodium bicarbonate (583 mg, 6.94 mmol). The solution was stirred at rt overnight and was then concentrated in vacuo. The dark residue was suspended in ethanol and heated at reflux for 15 minutes. The hot suspension was filtered, rinsing with hot ethanol, and the filtrate was concentrated in vacuo to afford 5,6-difluoro-1H-benzimidazol-2-amine (580 mg, 59%), which was used in the next step without further purification. LC-MS m/z 170.2 (MH+), ret. time 0.85 min; 1H NMR (300 MHz, DMSO-d6) δ 6.30 (br s, 2H), 7.06 (dd, 2H), 10.79 (br s, 1H).

後処理

  1. concentrationwas then concentrated in vacuo
  2. temperatureheated
  3. temperatureat reflux for 15 minutes
  4. filtrationThe hot suspension was filtered
  5. washrinsing with hot ethanol
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-3205d5ce1204465dacc8103cd5057f8c
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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