4-Chloro-2-toluidine → HCID 57756842, compound

HRID 228031Notes

Reaction equation

HRID 228031 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[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[CH3:32]>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][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])([CH2:8][CH2:9]2)[CH2:10][CH2:11]3)=[O:3])=[C:26]([CH3:32])[CH:27]=1

Participants

3

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756842HCID 57756842, compoundYield 24.3%

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 2-amino-5-chlorotoluene (48.2 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(4-chloro-2-methylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (16.8 mg).

Sources & evidence

ORD record
ord-67ab9b282bd649d4964f42f3771e5c19
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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