Sodium hydride → N-(2,4-dimethylphenyl)-N-isobutyl-4-((oxetan-3-ylmethoxy)methyl)benzenesulfonamide

HRID 1487052Notes

Reaction equation

[O:1]1[CH2:4][CH:3]([CH2:5][OH:6])[CH2:2]1.Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[CH3:30])[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[H-].[Na+]>CC1CCCO1>[CH3:30][C:24]1[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=1[N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:6][CH2:5][CH:3]2[CH2:4][O:1][CH2:2]2)=[CH:14][CH:13]=1)(=[O:17])=[O:16]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of oxetan-3-ylmethanol (7 mg, 0.075 mmol) and 4-(bromomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (31 mg, 0.075 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (1 mL) stirred under nitrogen at room temperature was added sodium hydride (60% dispersed in oil, approximately 2 mg, 0.075 mmol). The reaction mixture was stirred at 20° C. for 3 hours then quenched with water (75 uL). The solvent was removed under a stream of nitrogen to give the crude product. The crude was then purified by mass directed autoprep (ammonium carbonate modifier). The appropriate fractions were concentrated under a stream of nitrogen to give the required product, 2.4 mg. LCMS [LCMS1] Rt 1.34 min, m/z (ES+) 418 (M+H).

Workup

customthen quenched with water (75 uL)
customThe solvent was removed under a stream of nitrogen
customto give the crude product
customThe crude was then purified by mass
concentrationThe appropriate fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record: ord-766aeea53d47415395dc7f1c2c82b2c8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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