Tetrabutylammonium Fluoride → HCID 178424533, compound

HRID 1711248Notes

Reaction equation

HRID 1711248 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:14](COCC[Si](C)(C)C)[CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[NH2:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CO.C(Cl)Cl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58754865HCID 58754865, compound

Product 1

HCID 178424533HCID 178424533, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 24, step (b) using 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-carbamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 100 mg, 0.203 mmol) and tetrabutylammonium fluoride (1.01 mL, 1.01 mmol, 1.0 M in THF). Silica gel chromatography (5% MeOH/DCM) afforded the title compound (14.1 mg, 19%) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.42 (d, 1H, J=8.6 Hz), 8.00 (s, 1H), 7.81 (dd, 1H, J=8.6, 2.3 Hz), 7.75 (d, 1H, J=2.3 Hz), 5.81 (m, 1H), 2.28-2.40 (m, 2H), 2.04-2.17 (m, 2H), 1.63 (t, 2H, J=6.3 Hz), 1.11 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C20H21N5O2, 364.2 (M+H), found 364.1.

Workup

  1. customThe title compound was prepared by the procedure of Example 24, step (b)

Sources & evidence

ORD record
ord-1e0ebfe9ac074d6291fff0e9a348ef42
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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