4-Cyanobenzenesulfonyl chloride → HCID 71565861, compound

HRID 515122Notes

Reaction equation

HRID 515122 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:7][N:6]([CH2:8][C@@H:9]([C:11]2[C:12]([CH3:21])=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[O:15][CH2:14]3)[OH:10])[CH2:5]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(N(C(C)C)CC)(C)C>CN(C=O)C>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH:2][CH2:3][CH:4]2[CH2:7][N:6]([CH2:8][C@H:9]([OH:10])[C:11]3[C:12]([CH3:21])=[C:13]4[C:17](=[CH:18][CH:19]=3)[C:16](=[O:20])[O:15][CH2:14]4)[CH2:5]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1)#[N:23]

Participants

5

Reactant 3

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 90410636HCID 90410636, compound2×

Product 1

HCID 71565861HCID 71565861, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vial containing (R)-5-(2-(3-(aminomethyl)azetidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride [INTERMEDIATE 12] (0.17 g, 0.54 mmol) was added commercially available 4-cyanobenzene-1-sulfonyl chloride (0.20 g, 1.0 mmol) as a solution in DMF (500 μL) followed by diisopropylethylamine (0.16 g, 1.2 mmol). The vial was shaken for 24 hours, and then was concentrated in vacuo. The resulting residue was dissolved in DMSO (1 mL) and purified by HPLC to provide (R)-4-cyano-N-((1-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)azetidin-3-yl)methyl)benzenesulfonamide.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in DMSO (1 mL)
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-924888d629c344dcadcf7f099a093cbb
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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