HCID 58754829, compound → HCID 58754815, compound

HRID 1711266Notes

Reaction equation

HRID 1711266 reaction equation
[C:1]1([C:7]2[C:8]([NH2:16])=[CH:9][C:10]3[O:14][CH2:13][O:12][C:11]=3[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=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:1]1([C:7]2[C:8]([NH:16][C:33]([C:22]3[NH:21][C:20]([C:18]#[N:19])=[CH:24][N:23]=3)=[O:34])=[CH:9][C:10]3[O:14][CH2:13][O:12][C:11]=3[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 58754829HCID 58754829, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58754815HCID 58754815, compound

Procedure

The title compound was prepared by coupling 6-cyclohex-1-enyl-benzo[1,3]dioxol-5-ylamine (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 (DMSO-d6, 400 MHz): δ 14.23 (s, 1H), 9.67 (s, 1H), 8.31 (s, 1H), 7.48 (s, 1H), 6.78 (s, 1H), 6.01 (s, 2H), 5.69 (s, 1H), 2.20-2.05 (m, 4H), 1.71-1.57 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C18H16N4O3, 337.1 (M+H), found 337.0.

Sources & evidence

ORD record
ord-3628e03e2b5b45c7b2077f4e55ed9a0b
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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