Diisopropylethylamine → N-tert-butoxycarbonyl-N-(2-pyridinylmethyl)-N'-(1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-ylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 747331

Reaction equation

HRID 747331 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]2([CH3:28])[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:37][C:38]1[N:42]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[C:41]2[CH:51]=[CH:52][CH:53]=[CH:54][C:40]=2[N:39]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]([CH2:37][C:38]2[N:42]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:48])([CH3:49])[CH3:50])[C:41]3[CH:51]=[CH:52][CH:53]=[CH:54][C:40]=3[N:39]=2)[C:18]2([CH3:28])[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22018645N-tert-Butoxycarbonyl-N-(2-pyridinylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamineHCID 220187062-Chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole

Product 1

HCID 22018754N-tert-butoxycarbonyl-N-(2-pyridinylmethyl)-N'-(1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-ylmethyl)-N'-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamineYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of N-tert-Butoxycarbonyl-N-(2-pyridinylmethyl)-N′-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (120 mg, 0.26 mmol), 2-chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole (234 mg, 0.79 mmol) and diisopropylethylamine (229 μL, 1.31 mmol) in DMF (2.6 mL) for 18 h at 90° C. followed by purification of the crude material by radial chromatography (2 mm plate, 20:2:1 CHCl3—MeOH—NH4OH) afforded 90 mg (48%) of N-tert-butoxycarbonyl-N-(2-pyridinylmethyl)-N′-(1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-ylmethyl)-N′-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine as a colourless oil.

Workup

  1. customfollowed by purification of the crude material by radial chromatography (2 mm plate, 20:2:1 CHCl3—MeOH—NH4OH)

Sources & evidence

ORD record
ord-bae997fca7ec407ea7dec1f49788c4d9
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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