4-(1H-1,2,3,4-tetrazol-1-yl)benzene-1-sulfonyl chloride → 5-((R)-1-Hydroxy-2-((1S,4S)-5-(4-(1H-tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethyl)-4-methylisobenzofuran-1 (3H)-one

HRID 2281343Notes

Reaction equation

HRID 2281343 reaction equation
Cl.[C@@H:2]12[NH:9][C@@H:6](C[CH2:8]1)[CH2:5][N:4]([CH2:10][C@@H:11]([C:13]1[C:14]([CH3:23])=[C:15]3[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[O:17][CH2:16]3)[OH:12])[CH2:3]2.[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>>[OH:12][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)[CH2:10][N:4]1[CH2:3][C@@H:2]2[CH2:8][C@H:5]1[CH2:6][N:9]2[S:35]([C:32]1[CH:33]=[CH:34][C:29]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[CH:30][CH:31]=1)(=[O:37])=[O:36]

Participants

3

Reactant 2

HCID 433636414-(1H-1,2,3,4-tetrazol-1-yl)benzene-1-sulfonyl chlorideHCID 1176421335-((R)-2-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715570315-((R)-1-Hydroxy-2-((1S,4S)-5-(4-(1H-tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethyl)-4-methylisobenzofuran-1 (3H)-one

Procedure

5-((R)-1-Hydroxy-2-((1S,4S)-5-(4-(1H-tetrazol-1-yl)phenylsulfonyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)ethyl)-4-methylisobenzofuran-1 (3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 14 starting from 5-((R)-2-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride (INTERMEDIATE 15) and commercially available 4-(1H-tetrazol-1-yl)benzene-1-sulfonyl chloride.

Sources & evidence

ORD record
ord-177020d6f95c4f2fb38a23ffa71faf8d
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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