1-Chloro-4-methylphthalazine → 5-Amino-1-phenylbenzimidazole

HRID 1471339ノート

反応式

HRID 1471339 の反応式
ClC1C2C(=CC=CC=2)C(C)=NN=1.[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][C:24](C4C=CC=CC=4)=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1>CC(O)C>[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1

参加物

4

反応物 2

HCID 2697331-Chloro-4-methylphthalazineHCID 13024894HCID 13024894、化合物

生成物 1

HCID 9653125-Amino-1-phenylbenzimidazole収率 181.6%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 1-chloro-4-methylphthalazine (25 mg, 0.14 mmol) and 5-amino-1-(biphen-4-yl)benzimidazole (3) (28.5 mg, 0.10 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h, cooled to room temperature, and concentrated at reduced pressure. The residue is diluted with sat. NaHCO3 (15 mL) and extracted with CHCl3 (60 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (3.2% to 4.8% methanol/ethyl acetate) to give 38 mg (88%) of 4 (BI-3039) as a light-brown solid, mp 272-274° C. IR 3339, 2979, 1522, 1412 cm−1; 1H NMR (CD3OD/CDCl3) δ 2.82 (s, 3H, CH3), 7.36-7.53 (m, 3H, PhH), 7.62 (d, J=9.00 Hz, 1H, 7-BenzimidH), 7.69 (m, 2H, Aril, 2H PhH), 7.79 (d, J=8.7 Hz, 1H, 6-BenzimidH), 7.86 (d, J=8.1 Hz, 2H, ArH), 7.91-7.98 (m, 2H, 6,7-PhthH), 8.07 (m, 1H, 5-PhthH), 8.10 (s, 1H, 4-BenzimidH), 8.32 (s, 1H, 2-BenzimidH), 8.45 ppm (m, 1H, 8-PhthH).

後処理

  1. concentrationconcentrated at reduced pressure
  2. additionThe residue is diluted with sat. NaHCO3 (15 mL)
  3. extractionextracted with CHCl3 (60 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (3.2% to 4.8% methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-a243f4a8db75461eba0da2f8152b8a0e
出典データセット
uspto-grants-2015_04
特許番号
US09012217B2

反応ノート

読み込み中…