Benzenamine, 4-(phenylmethyl)- → (2s,4s)-4-Fluoro-1-[[n-[4-[n-(4-phenylmethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile

HRID 228008

Reaction equation

HRID 228008 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.[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1>>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:10][CH2:11][C:4]([C:1]([NH:37][C:34]4[CH:33]=[CH:32][C:31]([CH2:30][C:27]5[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=5)=[CH:36][CH:35]=4)=[O:3])([CH2:5][CH2:6]2)[CH2:9][CH2:8]3)[C@H:17]([C:22]#[N:23])[CH2:18]1

Participants

3

Reactant 2

HCID 136914Benzenamine, 4-(phenylmethyl)-HCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756732(2s,4s)-4-Fluoro-1-[[n-[4-[n-(4-phenylmethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrileYield 41.2%

Procedure

In a similar manner to Example 63, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and 4-aminodiphenylmethane (62.0 mg) were used to obtain (2S,4S)-4-fluoro-1-[[N-[4-[N-(4-phenylmethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile (31.1 mg).

Sources & evidence

ORD record
ord-220319b9474e4ba4aabb7ed93d6b27bd
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Linked notes

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