5-Methyl-1,3,4-oxadiazol-2-amine → (2S,4S)-4-fluoro-1-[[N-[4-[N-(5-methyl-1,3,4-oxadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile

HRID 228057Notes

Reaction equation

HRID 228057 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)(O)=[O:2].[NH2:24][C:25]1[O:26][C:27]([CH3:30])=[N:28][N:29]=1>>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:8][CH2:9][C:4]([C:1]([NH:24][C:25]4[O:26][C:27]([CH3:30])=[N:28][N:29]=4)=[O:2])([CH2:5][CH2:6]2)[CH2:11][CH2:10]3)[C@H:17]([C:22]#[N:23])[CH2:18]1

Participants

3

Reactant 2

HCID 20602505-Methyl-1,3,4-oxadiazol-2-amineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756751(2S,4S)-4-fluoro-1-[[N-[4-[N-(5-methyl-1,3,4-oxadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrileYield 23.2%

Procedure

In a similar manner to Example 87, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and 2-amino-5-methyl-1,3,4-oxadiazole (33.7 mg) were used to obtain (2S,4S)-4-fluoro-1-[[N-[4-[N-(5-methyl-1,3,4-oxadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile (14.5 mg).

Sources & evidence

ORD record
ord-8445b6cc6b7b4e81b221dc909978aa6e
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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