Ethyl Acetate → HCID 178424503, compound

HRID 1190219Notes

Reaction equation

C([Si](C)(C)[O:6][CH2:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[N:21](COCC[Si](C)(C)C)[CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[C:13]([C:35]2[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[CH2:37][CH:36]=2)[CH:12]=1)([CH3:10])[CH3:9])(C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[CH3:41][C:38]1([CH3:42])[CH2:39][CH2:40][C:35]([C:13]2[CH:12]=[C:11]([C:8]([CH3:9])([CH3:10])[CH2:7][OH:6])[CH:16]=[CH:15][C:14]=2[NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[CH:36][CH2:37]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 2.20 g, 3.45 mmol) and tetrabutylammonium fluoride hydrate (4.52 g, 17.3 mmol) in 25 mL of THF was stirred at 50° C. for 3 h. After cooling to RT, the mixture was treated with 100 mL of EtOAc and washed with saturated aqueous NH4Cl (20 mL), H2O (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (0-4% MeOH/DCM) to afford the title compound (1.25 g, 92%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C23H28N4O2, 393.2 (M+H). found 393.2.

Workup

temperatureAfter cooling to RT
washwashed with saturated aqueous NH4Cl (20 mL), H2O (20 mL) and brine (20 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (0-4% MeOH/DCM)

Sources & evidence

ORD record: ord-001f50f0e960470bbcd22dec8ffbb6a3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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