4-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride → HCID 89876238, compound

HRID 594145Notes

Reaction equation

HRID 594145 reaction equation
[CH:1]1([C:4]2[N:9]=[N:8][C:7]([NH2:10])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH3:11][C:12]1[C:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[C:15]([CH3:29])[O:14][N:13]=1>N1C=CC=CC=1>[CH:1]1([C:4]2[N:9]=[N:8][C:7]([NH:10][S:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:16]4[C:12]([CH3:11])=[N:13][O:14][C:15]=4[CH3:29])=[CH:24][CH:23]=3)(=[O:26])=[O:27])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 445581096-Cyclopropylpyridazin-3-amine

Product 1

HCID 89876238HCID 89876238, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-cyclopropylpyridazin-3-amine (50 mg, 0.370 mmol) in pyridine (1 mL), stirred under nitrogen at room temperature, was added 4-((3,5-dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride (346 mg, 1.147 mmol). The reaction mixture was stirred at room temperature for 16 hours. The mixture was evaporated and purified by solid phase extraction (SPE) using an aminopropyl (NH2) cartridge with sequential solvents methanol then 2M ammonia/methanol. The appropriate fractions were combined and evaporated in vacuo to give the crude product. The crude was further purified by mass directed autoprep (formic acid modifier). The relevant fractions were removed under a stream of nitrogen to give the title product (51 mg). LCMS (2 min, formic) Rt 0.86 min, m/z (ES+) 401 (M+H).

Workup

  1. customThe mixture was evaporated
  2. custompurified by solid phase extraction (SPE)
  3. customevaporated in vacuo
  4. customto give the crude product
  5. customThe crude was further purified by mass
  6. customThe relevant fractions were removed under a stream of nitrogen

Sources & evidence

ORD record
ord-73167d8722904e0988a61eade9fa6b80
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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