Tetrabutylammonium Fluoride → HCID 178421616, compound

HRID 1023658Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH3:19])[O:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[N:24](COCC[Si](C)(C)C)[CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH3:19])[O:14][CH2:15][CH2:16][CH2:17][O:18]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[NH:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 711626534-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxan-2-yl)-phenyl]-amide

Product 1

HCID 178421616HCID 178421616, compound

Procedure

The title compound was prepared from 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxan-2-yl)-phenyl]-amide (as prepared in the previous step, 145 mg, 0.276 mmol) and tetrabutylammonium fluoride (216 mg, 0.820 mmol) according to the procedure in Example 1, step (i) (69.4 mg, 64%). 1H-NMR (CDCl3; 400 MHz): δ 9.61 (s, 1H), 8.36 (d, 1H, J=8.4 Hz), 7.74 (s, 1H), 7.38 (dd, 1H, J=8.4, 1.9 Hz), 7.26 (m, 1H), 5.88 (s, 1H), 3.92-3.79 (m, 4H), 2.34-2.26 (m, 4H), 2.13 (m, 1H), 1.87-1.77 (m, 4H), 1.52 (s, 3H), 1.28 (m, 1H). Mass spectrum (ESI, m/z): Calcd. for C22H24N4O3, 393.1 (M+H), found 393.1.

Sources & evidence

ORD record: ord-d15a3d5e30cb4cfe8c35709566d3090a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722718B2

Reaction notes

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