Dichloromethane → HCID 178434596、化合物

HRID 44516

反応式

HRID 44516 の反応式
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:20]=[C:21]([C:22]#[N:23])[C:4]=2[N:3]=1.[C:30]([NH:33][NH2:34])(=O)[CH3:31].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(O)CCC.O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:20]=[C:21]([C:22]3[NH:34][N:33]=[C:30]([CH3:31])[N:23]=3)[C:4]=2[N:3]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 14039AcetohydrazideHCID 569596832-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carbonitrile

生成物 1

HCID 178434596HCID 178434596、化合物収率 26.1%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒

実験手順

To the suspension of 2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carbonitrile (120 mg, 0.314 mmol) in n-butanol (15 mL) was added in acetic hydrazide (232 mg, 3.14 mmol) and potassium carbonate (434 mg, 3.14 mmol). The reaction was stirred at reflux temperature for 4 days. DCM (50 mL) and water (50 mL) were added in. The organic phase was washed with Brine (50 mL×3), dried (MgSO4), and the solvent was removed. The crude was purified by reverse phase purification to provide the desired product (36 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.71 (br. s., 3H), 1.78 (br. s., 3H), 2.21-2.37 (m, 4H), 2.90-3.08 (m, 4H), 5.20 (s, 2H), 5.74 (d, J=7.33 Hz, 1H), 6.17 (br. s., 1H), 6.51 (t, J=7.71 Hz, 1H), 6.75-6.95 (m, 3H), 7.04 (d, J=8.08 Hz, 1H), 7.17 (d, J=8.08 Hz, 1H), 7.43 (d, 1H). MS (ES+) m/e 439.1[M+H]+.

後処理

  1. temperatureat reflux temperature for 4 days
  2. washThe organic phase was washed with Brine (50 mL×3)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed
  5. customThe crude was purified by reverse phase purification

出典と根拠

ORDレコード
ord-99c12c926beb47dc8986e8a4097d3256
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

関連ノート

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