Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate → (2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 228055Notes

Reaction equation

HRID 228055 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)([OH:3])=O.[NH2:24][C:25]1[S:29][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:27][N:26]=1>>[CH2:33]([O:32][C:30]([C:28]1[S:29][C:25]([NH:24][C:1]([C:4]23[CH2:9][CH2:8][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:6][CH2:5]2)[CH2:10][CH2:11]3)=[O:3])=[N:26][N:27]=1)=[O:31])[CH3:34]

Participants

3

Reactant 2

HCID 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylateHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756799(2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 43.1%

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 ethyl (5-amino-1,3,4-thiadiazole-2-carboxylate) (58.9 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (31.9 mg).

Sources & evidence

ORD record
ord-4ca57ffece0e4425a5a20b4045376281
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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