Methyl (1-(2-(4-(4-bromophenyl)-1H-imidazol-2-YL)pyrrolidin-1-YL)-3-methyl-1-oxobutan-2-YL)carbamate → (1-{2-[5-(6-Ethynyl-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

HRID 71931Notes

Reaction equation

HRID 71931 reaction equation
COC(=O)NC(C(N1CCCC1C1N[C:18]([C:21]2[CH:26]=CC(C#C)=[CH:23][CH:22]=2)=[CH:19]N=1)=O)C(C)C.[CH3:30][O:31][C:32](=[O:57])[NH:33][CH:34]([C:38]([N:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[NH:46][C:47]([C:50]2[CH:55]=[CH:54][C:53](Br)=[CH:52][CH:51]=2)=[CH:48][N:49]=1)=[O:39])[CH:35]([CH3:37])[CH3:36]>>[CH3:30][O:31][C:32](=[O:57])[NH:33][CH:34]([C:38]([N:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[NH:46][C:47]([C:50]2[CH:55]=[CH:54][C:53]3[C:52](=[CH:19][CH:18]=[C:21]([C:22]#[CH:23])[CH:26]=3)[CH:51]=2)=[CH:48][N:49]=1)=[O:39])[CH:35]([CH3:37])[CH3:36]

Participants

3

Reactant 2

HCID 66620141Methyl (1-(2-(4-(4-bromophenyl)-1H-imidazol-2-YL)pyrrolidin-1-YL)-3-methyl-1-oxobutan-2-YL)carbamate2×HCID 72338228(1-{2-[4-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Product 1

HCID 72338249(1-{2-[5-(6-Ethynyl-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Procedure

Title compound was prepared according to the method employed to prepare (1-{2-[5-(4-Ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester from (1-{2-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (Example AY), substituting (1-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester for (1-{2-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester.

Sources & evidence

ORD record
ord-f7ddcceecd9c4bdb810312ecc103738b
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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