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

반응식

HRID 7166 반응식
[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

참가 물질

5

반응물 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

생성물 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)-amine수율 67.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4a059695fa0041618a8dc164a748bfc6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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