Hydrochloric Acid → 2-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazole

HRID 392967Notes

Reaction equation

C[Al](C)C.[N:5]([Si](C)(C)C)=[N+:6]=[N-:7].[Si:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:29]3[CH:37]=[CH:38][C:39]([C:41]#[N:42])=[CH:40][C:28]=3[N:27]=2)=[CH:22][CH:21]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[N:30]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[C:29]3[CH:37]=[CH:38][C:39]([C:41]4[NH:7][N:6]=[N:5][N:42]=4)=[CH:40][C:28]=3[N:27]=2)=[CH:24][CH:25]=1)([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 95 °C

Procedure

Trimethylaluminum (20 mL of a 2.0 M solution in toluene, 0.040 mol) was added to a dry flask. Azidotrimethylsilane (5.3 mL, 0.040 mol) and compound 20 were added. The solution was stirred for 18 h at an oil bath temperature of 95° C. The solution was cooled and poured into a mixture of ethyl acetate and ice. The mixture was carefully acidified with dilute hydrochloric acid (caution-done in hood, hydrazoic acid liberated) to precipitate compound 21. The compound was crystallized from ethyl acetate—hexanes to afford 21 as a pinkish solid (4.13 g, 87%).

Workup

temperatureThe solution was cooled
customto precipitate compound 21
customThe compound was crystallized from ethyl acetate—hexanes

Sources & evidence

ORD record: ord-af2962750e6243d8b62f3b9b58d3c07a
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803374B2

Reaction notes

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