4-(Pyrrolidin-1-yl)aniline → (2S,4S)-1-[[N-[4-[N-[4-(pyrrolidin-1-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 228043Notes

Reaction equation

HRID 228043 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].[N:24]1([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1>>[N:24]1([C:29]2[CH:35]=[CH:34][C:32]([NH:33][C:1]([C:4]34[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]5[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]5[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]3)[CH2:6][CH2:5]4)=[O:2])=[CH:31][CH:30]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 8088414-(Pyrrolidin-1-yl)anilineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756856(2S,4S)-1-[[N-[4-[N-[4-(pyrrolidin-1-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 18.9%

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-(pyrrolidin-1-yl)aniline (50.2 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-[4-(pyrrolidin-1-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (13.7 mg).

Sources & evidence

ORD record
ord-41bd4979303d4b1abe5d79c1e0109aba
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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