4-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride → HCID 71543458, compound

HRID 1746429Notes

Reaction equation

HRID 1746429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][CH2:10][CH:11]([CH3:13])[CH3:12].[CH3:14][C:15]1[C:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[C:18]([CH3:32])[O:17][N:16]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:19]2[C:15]([CH3:14])=[N:16][O:17][C:18]=2[CH3:32])=[CH:27][CH:26]=1)(=[O:29])=[O:30]

Participants

4

Reactant 2

HCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 28974507HCID 28974507, compound

Product 1

HCID 71543458HCID 71543458, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2,6-difluorophenyl)(2-methylpropyl)amine (80 mg, 0.432 mmol) in pyridine (1 mL) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (156 mg, 0.518 mmol) and the reaction stood at room temperature, in air, for 16 hours. The solvent was removed in vacuo and the crude then passed through a sulfonic acid (SCX) SPE (solid phase extraction) cartridge eluting with methanol followed by 2M ammonia/methanol solution. The product-containing fractions were concentrated in vacuo and the crude then passed through an aminopropyl (NH2) SPE cartridge eluting with methanol followed by 2M ammonia/methanol solution. The appropriate fractions were combined and concentrated in vacuo, then further purified by MDAP (Method F) to give the required product, 0.6 mg. LCMS (M+18) 468, RT 1.28 mins.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe crude then passed through a sulfonic acid (SCX) SPE (solid phase extraction) cartridge
  3. washeluting with methanol
  4. concentrationThe product-containing fractions were concentrated in vacuo
  5. washeluting with methanol
  6. concentrationconcentrated in vacuo
  7. customfurther purified by MDAP (Method F)

Sources & evidence

ORD record
ord-4e15ecfc3db44339a64440fc0e32d9a6
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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