p-Toluenesulfonic acid → HCID 178523920, compound

HRID 2280414Notes

Reaction equation

HRID 2280414 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][NH:8]/[C:9](/[NH:20][C:21]2[NH:25][N:24]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:22]=2)=[N:10]/[C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:4][O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1COCC1>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][NH:8]/[C:9](/[NH:20][C:21]1[NH:25][N:24]=[C:23]([C:26]([F:27])([F:29])[F:28])[CH:22]=1)=[N:10]/[C:11](=[O:19])[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 178431434HCID 178431434, compound

Product 1

HCID 178523920HCID 178523920, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)—N-((((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amino)((3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)methylene)-4-fluorobenzamide (300 mg) in THF (7 mL) was added para-toluenesulfonic acid (p-TsOH) (133 mg, 1 equiv). The reaction mixture was shaken at room temperature overnight. The solution was then treated with triethylamine (100 μL), concentrated onto silica gel, and purified by silica chromatography (3:1 hexanes:EtOAc to EtOAc) to provide the title compound (115 mg (91% purity), 42% yield). MS (EI+) m/z: 389.93, 411.89; HPLC (Method B): 5.19 min

Workup

  1. concentrationconcentrated onto silica gel
  2. custompurified by silica chromatography (3:1 hexanes:EtOAc to EtOAc)

Sources & evidence

ORD record
ord-7fc15a1d499a41a0b50c6eadfed65a93
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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