[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 1508111Notes

Reaction equation

HRID 1508111 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-ba7f88099505474dbd0b356b18f4e26f
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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