4-Cyanobenzenesulfonyl chloride → HCID 71559229, compound

HRID 2281339Notes

Reaction equation

HRID 2281339 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Cl.[C@H:14]12[CH2:20][C@H:17]([NH:18][CH2:19]1)[CH2:16][N:15]2[CH2:21][C@@H:22]([C:24]1[C:25]([CH3:34])=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][CH2:27]2)[OH:23].CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[OH:23][C@H:22]([C:24]1[C:25]([CH3:34])=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][CH2:27]2)[CH2:21][N:15]1[CH2:16][C@@H:17]2[CH2:20][C@H:14]1[CH2:19][N:18]2[S:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 117642154HCID 117642154, compound2×

Product 1

HCID 71559229HCID 71559229, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-cyanobenzene-1-sulfonyl chloride (31 mg, 0.12 mmol) in 0.3 mL of DMF was added to a solution of 5-((R)-2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride (32 mg, 0.10 mmol) (INTERMEDIATE 14) in 0.2 mL of DMF and DIEA (87 uL, 0.50 mmol). The combined solution was shaken for sixteen hours and then diluted with 0.5 mL DMSO. The resulting solution was purified by HPLC to afford 4-((1S,4S)-5-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-2,5-diazabicyclo[2.2.1]heptan-2-ylsulfonyl)benzonitrile.

Workup

  1. customThe resulting solution was purified by HPLC

Sources & evidence

ORD record
ord-f4bd2907e6c544de80a268cb531b04b7
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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