2-(4-Aminophenyl)benzothiazole → (2S,4S)-1-[[N-[4-[N-[4-(benzothiazol-2-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 228042

Reaction equation

HRID 228042 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.[S:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1>>[S:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[C:33]1[CH:39]=[CH:38][C:36]([NH:37][C:1]([C:4]23[CH2:5][CH2:6][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])([CH2:10][CH2:11]2)[CH2:8][CH2:9]3)=[O:3])=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 2344752-(4-Aminophenyl)benzothiazoleHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756769(2S,4S)-1-[[N-[4-[N-[4-(benzothiazol-2-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 12.7%

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-(benzothiazol-2-yl)aniline (51.0 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-[4-(benzothiazol-2-yl)phenyl]amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (10.4 mg).

Sources & evidence

ORD record
ord-ed64cc21e8e64848adb9b24729f6ac73
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Linked notes

Loading…