p-Toluenesulfonic acid → HCID 68903059, compound

HRID 1436454Notes

Reaction equation

HRID 1436454 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:9]=1.CO[C:20](OC)([CH3:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:21][C:20]1([CH3:22])[N:4]([C:5]2[S:6][CH:7]=[C:8]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)[N:9]=2)[CH2:3][CH2:2][O:1]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 86618619HCID 86618619, compound

Product 1

HCID 68903059HCID 68903059, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-{2-[(2-hydroxyethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.0 g, 4.0 mmol), prepared in the previous step, 2,2-dimethoxypropane (7.2 mL, 61.2 mmol) and a catalytic amount of p-toluenesulfonic acid in toluene (90 mL) was heated at 90° C. overnight. The reaction was cooled and concentrated to a residue. Purification of the crude product on silica gel using 5% ethyl acetate:hexane as the eluent gave 480 mg of impure product. Final purification by reverse phase HPLC using an isocratic system of 80:20 acetonitrile:water gave the title compound (107 mg, 10%), mp 108-111° C.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated to a residue
  3. customPurification of the crude product on silica gel using 5% ethyl acetate

Sources & evidence

ORD record
ord-37929e72b1fb4034b137f6429acd556e
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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