4-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride → HCID 89875971, compound

HRID 594140Notes

Reaction equation

HRID 594140 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH2:10])=[CH:6][N: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]=[CH: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][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 431422352-Cyclopropylpyrimidin-5-amine

Product 1

HCID 89875971HCID 89875971, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-cyclopropylpyrimidin-5-amine (50 mg, 0.370 mmol) in pyridine (1 mL) stirred in air at room temperature was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (123 mg, 0.407 mmol). The reaction mixture was stirred at 20° C. for 30 minutes, to ensure dissolution and then left to stand overnight. The solvent was evaporated in vacuo to give the crude product which was purified by mass directed autoprep (formic acid modifier) to give the title product (74.5 mg). LCMS (2 min, formic) Rt 0.94 min, m/z (ES+) 401 (M+H).

Workup

  1. dissolutiondissolution
  2. waitleft
  3. waitto stand overnight
  4. customThe solvent was evaporated in vacuo
  5. customto give the crude product which
  6. customwas purified by mass

Sources & evidence

ORD record
ord-aa5dbfa857204d899d58e420e104c68c
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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