Water → HCID 59742752, compound

HRID 1946974Notes

Reaction equation

[C:1]([N:20]1[CH:24]=[C:23]([NH:25][C:26](=O)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:26]([NH:25][C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-(1-trityl-1H-imidazol-4-yl)-benzamide (0.36 g, 0.83 mmol) in tetrahydrofuran (10 ml) was added portionwise lithium aluminium hydride (0.16 g, 4.14 mmol). The reaction mixture was stirred at 80° C. for 16 hours, then cooled to room temperature and water added dropwise. The mixture was stirred at room temperature for 20 minutes and then extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane 0:100 to 10:90) to yield the title compound as a white solid (0.15 g, 44%); MS (ISP): 416.5 ([M+H]+).

Workup

temperaturecooled to room temperature
stirringThe mixture was stirred at room temperature for 20 minutes
extractionextracted with ethyl acetate
customThe organic layer was separated
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane 0:100 to 10:90)

Sources & evidence

ORD record: ord-0900abbdf9c1461094a279247018ab58
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399463B2

Reaction notes

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