5-Amino-1-phenylbenzimidazole → HCID 59373121、化合物

HRID 1471338ノート

反応式

HRID 1471338 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=1.[NH2:17][C:18]1[CH:32]=[CH:31][C:21]2[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[N:24][C:20]=2[CH:19]=1>CC(O)C>[C:25]1([N:22]2[C:21]3[CH:31]=[CH:32][C:18]([NH:17][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=4)=[CH:19][C:20]=3[N:24]=[CH:23]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

4

反応物 2

HCID 9653125-Amino-1-phenylbenzimidazoleHCID 59372952HCID 59372952、化合物

生成物 1

HCID 59373121HCID 59373121、化合物収率 28.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 1-chloro-4-(prop-2-ynyloxy)methylphthalazine (3) (20 mg, 0.09 mmol) and 5-amino-1-phenylbenzimidazole (15 mg, 0.07 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h. The reaction mixture is concentrated, quenched with sat. NaHCO3 (10 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 (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane) to give 8 mg (27%) of BI-3035 as a light-brown solid, mp 89-91° C. IR 3321, 2927, 1496 cm−1; 1H NMR (CDCl3) δ 2.60 (t, J=2.4 Hz, 1H, CH≡C—CH2O), 4.98 (s, 2H, CH2), 5.36 (d, J=2.4 Hz, CH≡CCH2O), 6.94 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.27 (d, J=2.1 Hz, 1H, 4-BenzimidH), 7.41 (d, J=8.7 Hz, 1H, 7-BenzimidH), 7.41-7.63 (m, 5H, PhH), 7.90-8.02 (m, 2H, 6,7-PhthH), 8.06 (s, 1H, 2-BenzimidH), 8.14 (m, 1H, 5-PhthH), 8.35 (m, 1H, 8-PhthH).

後処理

  1. concentrationThe reaction mixture is concentrated
  2. customquenched with sat. NaHCO3 (10 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 (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-75c31f9cac3947318e91b669617d3351
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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