2-bromo-N-(isoxazol-3-yl)acetamide → 4-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

HRID 1690657Notes

Reaction equation

HRID 1690657 reaction equation
[Br-].[OH:2][C:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:4]([O:6][CH:7]1[CH2:12][CH2:11][N+:10]([CH2:14][C:15](=[O:22])[NH:16][C:17]2[CH:21]=CO[N:18]=2)([CH3:13])[CH2:9][CH2:8]1)=[O:5].[Br:35][CH2:36][C:37]([NH:39]C1C=CON=1)=O.BrCC(NC1C=NC=CN=1)=O>>[Br-:35].[OH:2][C:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:4]([O:6][CH:7]1[CH2:12][CH2:11][N+:10]([CH3:13])([CH2:14][C:15](=[O:22])[NH:16][C:17]2[CH:21]=[N:39][CH:37]=[CH:36][N:18]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

4

Reactant 3

HCID 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 445426692-bromo-N-(pyrazin-2-yl)acetamide2×HCID 866342234-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

Product 1

HCID 866342254-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-piperidinium bromide

Procedure

This compound is prepared by an analogous method to 4-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide (Example 13) by replacing 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) with 2-bromo-N-pyrazin-2-yl-acetamide (Intermediate G).

Sources & evidence

ORD record
ord-759a1b8d757245798d17cc014c2ef7f6
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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