5-Benzimidazolecarboxylic acid → HCID 178418743、化合物

HRID 8964

反応式

HRID 8964 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](O)=[O:17])=[CH:15][C:10]=2[NH:9][CH:8]=1>C1COCC1.C(Cl)Cl.CO.[O-2].[Mn+4].[O-2]>[NH:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=[O:17])=[CH:15][C:10]=2[N:9]=[CH:8]1

参加物

7

反応物 2

HCID 4594565-Benzimidazolecarboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 178418743HCID 178418743、化合物収率 60%

試薬・触媒・溶媒 4

HCID 178418406HCID 178418406、化合物触媒HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

LiAlH4 (1.0 m in THF, 10 mL, 10 mmol) was added dropwise to a suspension of 5-benzimidazolecarboxylic acid (500 mg, 3.08 mmol) in THF (20 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 24 h followed by heating at 50° C. for an addition 24 h. MeOH (4×5 mL) was added and the solution was concentrated between each addition. The resulting brown syrup was dried in vacuo for 3 h. The syrup was dissolved in 100:1—CH2Cl2:MeOH, filtered through celite and concentrated to a light brown foam (300 mg, 66%). To a stirred solution of the crude alcohol (300 mg, 2.0 mmol) in CH2Cl2 (10 mL) and MeOH (0.8 mL) was added manganese (IV) oxide (85%, 2.05 g, 20 mmol). The suspension was heated to 40° C. for 18 h, cooled to room temperature and filtered through celite. The filtrant was concentrated to a light yellow foam (260 mg). Purification of the crude material by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH) gave the title compound as a white powder (139 mg, 60%). 1H NMR (300 MHz, CD3OD) δ 10.0 (s, 1H), 8.38 (s, 1H), 8.20 (s, 1H), 7.87 (d, 1H, J=9.0 Hz), 7.75 (d, 1H, J=9.0 Hz).

後処理

  1. temperatureby heating at 50° C. for an addition 24 h
  2. concentrationthe solution was concentrated between each addition
  3. customThe resulting brown syrup was dried in vacuo for 3 h
  4. dissolutionThe syrup was dissolved in 100
  5. filtration1—CH2Cl2:MeOH, filtered through celite
  6. concentrationconcentrated to a light brown foam (300 mg, 66%)
  7. temperatureThe suspension was heated to 40° C. for 18 h
  8. temperaturecooled to room temperature
  9. filtrationfiltered through celite
  10. concentrationThe filtrant was concentrated to a light yellow foam (260 mg)
  11. customPurification of the crude material by column chromatography on silica gel (200:1:1—EtOAc:MeOH:NH4OH)

出典と根拠

ORDレコード
ord-b9008a354c184d54bf57d34ec3e39e40
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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