1-Chloro-4-phenylphthalazine → HCID 1386209、化合物

HRID 1471331ノート

反応式

HRID 1471331 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[NH2:18][C:19]1[CH:33]=[CH:32][C:22]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=[N:25][C:21]=2[CH:20]=1>CC(O)C>[C:26]1([N:23]2[C:22]3[CH:32]=[CH:33][C:19]([NH:18][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:20][C:21]=3[N:25]=[CH:24]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

4

反応物 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 9653125-Amino-1-phenylbenzimidazole

生成物 1

HCID 1386209HCID 1386209、化合物収率 99.6%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 1-chloro-4-phenylphthalazine (156 mg, 0.65 mmol) and 5-amino-1-phenylbenzimidazole (4) (105 mg, 0.5 mmol) in i-PrOH (10 mL) is stirred at 95° C. under argon for 2 h. The reaction mixture is concentrated, diluted with sat. NaHCO3 (15 mL), and extracted with CHCl3 (100 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (1% to 9% methanol/ethyl acetate) to give 206 mg (99%) of 5 as an orange solid, mp 265° C. IR 3285, 2842, 1615, 1476 cm−1; 1H NMR (CDCl3) δ 7.45-7.61 (m, 5H, 1-PhH), 7.62-7.77 (m, 6H, 4′-C6H5, 7-BenzimidH), 7.82 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.86-7.90 (m, 1H, 5′-PhthH), 7.91-7.98 (m, 1H, 6′-PhthH), 8.00-8.08 (m, 1H, 7′-PhthH), 8.50 (d, J=2.1 Hz, 1H, 4-BenzimidH), 8.56 (s, 1H, 2-BenzimidH), 8.72 (d, J=8.7 Hz, 1H, 8′-PhthH), 9.37 ppm (s, 1H, NH).

後処理

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with sat. NaHCO3 (15 mL)
  3. extractionextracted with CHCl3 (100 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (1% to 9% methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-4c937f03d04c4d04957890f17d701a28
出典データセット
uspto-grants-2015_04
特許番号
US09012217B2

反応ノート

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