Sodium borohydride → (1H-Benzimidazol-2-ylmethyl)-(4-{[(1H-benzimidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7175

反応式

HRID 7175 の反応式
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=O.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][N:30]([CH:40]1[C:49]2[N:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH2:43][CH2:42][CH2:41]1)[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[CH:34][CH:33]=1.[BH4-].[Na+]>CO>[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][N:30]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH:39][CH2:16][C:8]2[NH:7][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)=[CH:34][CH:33]=1)[CH:40]1[C:49]2[N:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH2:43][CH2:42][CH2:41]1

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 120171281-(2-Trimethylsilylethoxymethyl)-2-formyl-benzimidazoleHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 22018638(1H-Benzimidazol-2-ylmethyl)-(4-{[(1H-benzimidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine収率 47%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of 1-(2-trimethylsilylethoxymethyl)-2-formyl-benzimidazole (prepared as described by Bridger et al. U.S. patent application Ser. No. 09/535,314) (0.150 g, 0.54 mmol) in dry MeOH (2.5 mL) was added a dry MeOH (2.5 mL) solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.215 g, 0.54 mmol) under an argon atmosphere. The mixture was stirred at room temperature for 1.5 h then concentrated under reduced pressure and analyzed by 1H NMR. The residue was dissolved in dry MeOH (5 mL) and to the resultant solution was added sodium borohydride (41 mg, 1.08 mmol) and the reaction mixture stirred for 16 h (see General Procedures XX). Purification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1) afforded the desired product (0.165 g, 47%) as a pale yellow oil.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dry MeOH (5 mL) and to the resultant solution
  3. stirringthe reaction mixture stirred for 16 h (see General Procedures XX)
  4. customPurification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1)

出典と根拠

ORDレコード
ord-0ff3ba42618041fc8e5a90fd6e987d41
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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