[5-Amino-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester → [5-[(5-Cyano-1H-imidazole-2-carbonyl)-amino]-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester

HRID 1190176Notes

Reaction equation

HRID 1190176 reaction equation
[K+].[C:2]([C:4]1[N:5]=[C:6]([C:17]([O-:19])=O)[N:7](COCC[Si](C)(C)C)[CH:8]=1)#[N:3].[CH2:20]([O:22][C:23](=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([C:32]2[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH:33]=2)[N:26]=1)[CH3:21]>>[CH2:20]([O:22][C:23](=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:17]([C:6]2[NH:5][C:4]([C:2]#[N:3])=[CH:8][N:7]=2)=[O:19])=[C:27]([C:32]2[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH:33]=2)[N:26]=1)[CH3:21]

Participants

3

Reactant 2

HCID 58994431[5-Amino-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl esterHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 24875127[5-[(5-Cyano-1H-imidazole-2-carbonyl)-amino]-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester

Procedure

The title compound was prepared by coupling 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 1, step (d)) and [5-amino-6-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-acetic acid ethyl ester (as prepared in the previous step) according to the procedure in Example 34, step (c), followed by SEM deprotection according to the procedure in Example 34, step (d). Mass spectrum (ESI, m/z): Calcd. for C22H25ClN5O3, 408.2 (M+H). found 408.2.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-9c124cca3e8b4b1dab5904296be3edaf
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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