HCID 58754883, compound → HCID 24759285, compound

HRID 1711264Notes

Reaction equation

HRID 1711264 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1.[K+].[C:18]([C:20]1[N:21]=[C:22]([C:33]([O-])=[O:34])[N:23](COCC[Si](C)(C)C)[CH:24]=1)#[N:19]>>[C:11]1([C:3]2[CH:4]=[C:5]([CH2:8][CH2:9][OH:10])[CH:6]=[CH:7][C:2]=2[NH:1][C:33]([C:22]2[NH:21][C:20]([C:18]#[N:19])=[CH:24][N:23]=2)=[O:34])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

3

Reactant 2

HCID 58754883HCID 58754883, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 24759285HCID 24759285, compound

Procedure

The title compound was prepared by coupling 2-(4-amino-3-cyclohex-1-enyl-phenyl)-ethanol (prepared in the previous step) and 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (prepared in Example 11, step (d)) according to the procedure in Example 42, step (c) followed by SEM deprotection according to the procedure in Example 11, step (g). 1H-NMR (CD3OD, 400 MHz): δ 8.10 (d, J=8.3 Hz, 1H), 8.02 (s, 1H), 7.17 (dd, J=8.3, 1.9 Hz, 1H), 7.08 (d, J=1.9 Hz, 1H), 5.82 (s, 1H), 3.77 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.0 Hz, 2H), 2.31-2.25 (m, 4H), 1.90-1.76 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C19H20N4O2, 337.2 (M+H), found 337.1.

Sources & evidence

ORD record
ord-8cd1f7a126d544c68551808acde6b6ae
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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