HCID 14661996, compound → HCID 71543682, compound

HRID 1746398Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([NH:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:13][C:14]1[C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[C:17]([CH3:31])[O:16][N:15]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([N:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[S:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:18]3[C:14]([CH3:13])=[N:15][O:16][C:17]=3[CH3:31])=[CH:26][CH:25]=2)(=[O:28])=[O:29])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(4-chlorophenyl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide was prepared in an array format. 4-chloro-N-isobutylaniline (1.493 mg, 0.099 mmol) was pre-weighed into a 2 mL vial, and 4-((3,5-dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride (30 mg, 0.099 mmol) then added, followed by 4-DMAP (approx 2 mg). Pyridine (0.3 mL) was added last. The reaction solution was capped and stood at RT for 3 days. After this time the reaction was not complete and the reaction were warmed to 80° C. for 2 hours. The pyridine was removed to almost dryness. DMSO (1 mL) was added to the residues which were then purified by mass directed autoPrep on a Sunfire C18 column using Acetonitrile Water with a Formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required products.

Workup

customThe reaction solution was capped
customThe pyridine was removed to almost dryness
additionDMSO (1 mL) was added to the residues which
customwere then purified by mass
customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record: ord-94818843f3ec4704b4e8629095ad4fde
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

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