1-Methyl-2-imidazolecarboxaldehyde → (1h-Benzoimidazol-2-ylmethyl)-(4-{[(1-methyl-1h-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7166

反応式

HRID 7166 の反応式
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[NH2:9][CH2:10][C:11]1[CH:38]=[CH:37][C:14]([CH2:15][N:16]([CH2:27][C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)[CH:17]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[BH4-].[Na+]>CO>[NH:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[CH2:27][N:16]([CH2:15][C:14]1[CH:37]=[CH:38][C:11]([CH2:10][NH:9][CH2:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)=[CH:12][CH:13]=1)[CH:17]1[C:26]2[N:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:20][CH2:19][CH2:18]1

参加物

5

反応物 3

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 4311764Sodium borohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 20763961(1h-Benzoimidazol-2-ylmethyl)-(4-{[(1-methyl-1h-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine収率 67.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Using General Procedure B: A solution of 1-methyl-2-imidazole carboxaldehyde (27.5 mg, 0.25 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (37.5, 0.75 mmol) was added and the resultant mixture stirred for an additional 15 minutes. Purification of the crude white foam by column chromatography on silica gel (CH2Cl2[MeOH/NH4OH, 50:1:1) followed by radial chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 200:3:2) afforded the desired amine (83 mg, 67%) as a white foam.

後処理

  1. customPurification of the crude white foam by column chromatography on silica gel (CH2Cl2[MeOH/NH4OH, 50:1:1)

出典と根拠

ORDレコード
ord-4a059695fa0041618a8dc164a748bfc6
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

関連ノート

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