Benzocaine → HCID 57756812, compound

HRID 228065Notes

Reaction equation

HRID 228065 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:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1>>[CH2:32]([O:31][C:29]([C:28]1[CH:27]=[CH:26][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])([CH2:10][CH2:11]2)[CH2:6][CH2:5]3)=[O:3])=[CH:35][CH:34]=1)=[O:30])[CH3:33]

Participants

3

Reactant 2

HCID 2337BenzocaineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756812HCID 57756812, compoundYield 34.2%

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 ethyl 4-aminobenzoate (56.0 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(4-ethoxycarbonylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (24.9 mg).

Sources & evidence

ORD record
ord-2941cd2b1e0642368ad84667c1bd8621
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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