2-Amino-5-methylpyridine → 4-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide

HRID 594126

Reaction equation

HRID 594126 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[C:13]([CH3:27])[O:12][N:11]=1>N1C=CC=CC=1>[CH3:9][C:10]1[C:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[C:13]([CH3:27])[O:12][N:11]=1

Participants

4

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride

Product 1

HCID 898762704-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-methylpyridin-2-amine (54 mg, 0.5 mmol) in pyridine (5 mL) stirred at room temperature, was added 4-((3,5-dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride (0.151 g, 0.5 mmol). The reaction was stirred at room temperature overnight. The solvent was then removed under a stream of nitrogen to give the crude product, which was used directly in the next reaction with no purification. LCMS (2 min, formic) Rt 0.84 min, m/z (ES+) 374 (M+H).

Workup

  1. customThe solvent was then removed under a stream of nitrogen

Sources & evidence

ORD record
ord-fe04bd9e1d29409283c77f5f798058d3
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Linked notes

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