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

関与物質

役割	名称	HCID	仕込み量
反応物	1-Methyl-2-imidazolecarboxaldehyde	HCID 139575	—
反応物	Sodium borohydride	HCID 4311764	—
反応物	N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine	HCID 21985008	—
溶媒	Methanol	HCID 887	—
生成物	(1h-Benzoimidazol-2-ylmethyl)-(4-{[(1-methyl-1h-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine	HCID 20763961	67.5%

反応手順

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.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07084155B2
出典データセット	uspto-grants-2006_08
ORD ID	ord-4a059695fa0041618a8dc164a748bfc6
出典メモ	uspto-grants-2006_08