Indole-2-carboxaldehyde → n1-(1h-Benzimidazol-2-ylmethyl)-n4-(1h-indol-2-ylmethyl)-n1-(5,6,7,8-tetrahydroquinolin-8-yl)-butane-1,4-diamine

HRID 899602ノート

反応式

HRID 899602 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=O.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][N:22]([CH:28]1[C:37]2[N:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH2:31][CH2:30][CH2:29]1)[CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].[BH4-].[Na+]>CO>[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][N:22]([CH:28]1[C:37]2[N:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH2:31][CH2:30][CH2:29]1)[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:10][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

参加物

5

反応物 3

HCID 96389Indole-2-carboxaldehyde2 回HCID 4311764Sodium borohydrideHCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine2 回

生成物 1

HCID 10217440n1-(1h-Benzimidazol-2-ylmethyl)-n4-(1h-indol-2-ylmethyl)-n1-(5,6,7,8-tetrahydroquinolin-8-yl)-butane-1,4-diamine収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of indole-2-carboxaldehyde (prepared as described for COMPOUND 65) (31 mg, 0.21 mmol) and N1-(1H-benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydroquinolin-8-yl)-butane-1,4-diamine (see COMPOUND 17) (51 mg, 0.15 mmol) in MeOH (1.8 mL) was stirred at room temperature under nitrogen for 23 hours. NaBH4 (14 mg, 0.37 mmol) was added, and the reaction stirred for a further 15 minutes before the solvent was evaporated under reduced pressure. The residue was dissolved into CH2Cl2 (25 mL) and was washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic solution was dried (MgSO4), filtered and evaporated under reduced pressure. The yellow residue was purified by flash column chromatography on silica gel (CH2Cl2MeOH/NH4OH, 19:1:0.1) giving COMPOUND 31 as a white solid (37 mg, 0.077 mmol, 53%). 1H NMR (CDCl3) δ 1.35-1.49 (m, 4H), 1.60-1.76 (m, 1H), 1.81-1.96 (m, 1H), 1.96-2.08 (m, 1H), 2.11-2.22 (m, 1H), 2.45 (t, 2H, J=6.5 Hz), 2.50-2.60 (m, 1H), 2.66-2.76 (m, 2H), 2.76-2.90 (m, 1H), 3.83 (s, 2H), 3.93-4.10 (m, 3H), 6.27 (s, 1H), 7.02-7.16 (m, 3H), 7.16-7.24 (m, 2H), 7.32 (d, 1H, J=7.8 Hz), 7.41 (d, 1H, J=7.8 Hz), 7.53 (d, 1H, J=7.8 Hz), 7.55-7.62 (m, 2H), 8.56 (d, 1H, J=3.6 Hz), 9.01 (br. s, 1H). 13C NMR (CDCl3) δ 21.6, 23.8, 26.2, 27.5, 29.6, 47.2, 48.9, 49.8, 50.8, 62.3, 100.6, 111.2, 119.8, 120.4, 121.7, 122.0, 122.6, 128.8, 135.1, 136.5, 137.8, 147.1, 156.9, 157.8. ES-MS m/z 479 (M+H). Anal. Calcd. for C30H34N6.0.5CH2Cl2.0.2C4H10O: C, 70.15; H, 6.96; N, 15.68. Found: C, 70.16; H, 6.97; N, 15.73.

後処理

  1. customwas evaporated under reduced pressure
  2. dissolutionThe residue was dissolved into CH2Cl2 (25 mL)
  3. washwas washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe yellow residue was purified by flash column chromatography on silica gel (CH2Cl2MeOH/NH4OH, 19:1:0.1)

出典と根拠

ORDレコード
ord-f18c73a226dc468993174c3cfad92f7a
出典データセット
uspto-grants-2008_04
特許番号
US07354932B2

反応ノート

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