4-Hydroxymethylpyridine → N-(2,4-dimethylphenyl)-N-isobutyl-4-(pyridine-4-ylmethoxy)benzenesulfonamide

HRID 1746405Notes

Reaction equation

HRID 1746405 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:30][C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 71543523N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide

Product 1

HCID 71543524N-(2,4-dimethylphenyl)-N-isobutyl-4-(pyridine-4-ylmethoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide (33 mg, 0.099 mmol), pyridine-4ylmethanol (2.52 mg, 0.148 mmol), triphenylphosphine (39 mg, 0.149 mmol) were pre-weighed into a 4 mL glass vial. Tetrahydrofuran (THF) (0.6 mL) was added followed by diisopropyl diazene-1,2-dicarboxylate (DIAD) (0.029 mL, 0.148 mmol). The vial was capped and stirred at RT for 2 days. The reaction mixture was filtered to remove any insoluble materials. The sample was purified by mass directed autoprep on an Xbridge column using acetonitrile:water with an ammonium carbonate modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product.

Workup

  1. customThe vial was capped
  2. filtrationThe reaction mixture was filtered
  3. customto remove any insoluble materials
  4. customThe sample was purified by mass
  5. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-f943437f7d684f46837b27bcd0da421e
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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