4-(1H-1,2,3,4-tetrazol-1-yl)benzene-1-sulfonyl chloride → 5-((1R)-2-(5-(4-(1H-Tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.2]octan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1 (3H)-one

HRID 2281344Notes

Reaction equation

HRID 2281344 reaction equation
Cl.[CH:2]12[CH2:9][CH2:8][CH:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[CH2:10][C@@H:11]([C:13]1[C:14]([CH3:23])=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[O:17][CH2:16]2)[OH:12].[N:24]1([C:29]2[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH:28]=[N:27][N:26]=[N:25]1>>[N:24]1([C:29]2[CH:30]=[CH:31][C:32]([S:35]([N:6]3[CH2:7][CH:2]4[CH2:9][CH2:8][CH:5]3[CH2:4][N:3]4[CH2:10][C@@H:11]([C:13]3[C:14]([CH3:23])=[C:15]4[C:19](=[CH:20][CH:21]=3)[C:18](=[O:22])[O:17][CH2:16]4)[OH:12])(=[O:37])=[O:36])=[CH:33][CH:34]=2)[CH:28]=[N:27][N:26]=[N:25]1

Participants

3

Reactant 2

HCID 433636414-(1H-1,2,3,4-tetrazol-1-yl)benzene-1-sulfonyl chlorideHCID 1176420755-((1R)-2-(2,5-diazabicyclo[2.2.2]octan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715571825-((1R)-2-(5-(4-(1H-Tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.2]octan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1 (3H)-one

Procedure

5-((1R)-2-(5-(4-(1H-Tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.2]octan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1 (3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 14 starting from 5-((1R)-2-(2,5-diazabicyclo[2.2.2]octan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride (INTERMEDIATE 16) and commercially available 4-(1H-tetrazol-1-yl)benzene-1-sulfonyl chloride.

Sources & evidence

ORD record
ord-ec11fb482c4a4817a673cdd3e2d0548c
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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