4-Cyanobenzenesulfonyl chloride → 4-Cyano-N-((R)-1-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)pyrrolidin-3-yl)benzenesulfonamide

HRID 515123Notes

Reaction equation

HRID 515123 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]([C:11]2[CH:20]=[CH:19][C:14]3[C:15](=[O:18])[O:16][CH2:17][C:13]=3[C:12]=2[CH3:21])[OH:10])[CH2:4]1.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)#[N:23]>>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH:2][C@@H:3]2[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]([OH:10])[C:11]3[C:12]([CH3:21])=[C:13]4[C:14](=[CH:19][CH:20]=3)[C:15](=[O:18])[O:16][CH2:17]4)[CH2:4]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1)#[N:23]

Participants

3

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 901903035-{(1R)-2-[(3R)-3-aminopyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715658624-Cyano-N-((R)-1-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)pyrrolidin-3-yl)benzenesulfonamide

Procedure

4-Cyano-N—((R)-1-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)pyrrolidin-3-yl)benzenesulfonamide was prepared in a similar fashion to that described for the synthesis of EXAMPLE 14 starting from 5-{(1R)-2-[(3R)-3-Aminopyrrolidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 4] and 4-cyanobenzene-1-sulfonyl chloride.

Sources & evidence

ORD record
ord-b734649a893049b4a90e98899a36bf59
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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