4-Tert-Butylaniline → N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide

HRID 38090

Reaction equation

HRID 38090 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19](O)=[O:20])=[N:10][N:11]3[CH2:15][CH2:14][S:13][C:12]=23)=[CH:4][CH:3]=1.[C:25]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>S(Cl)(Cl)=O.C(OCC)(=O)C>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([NH:33][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([C:9]3[C:8]([C:5]4[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=4)=[C:12]4[S:13][CH2:14][CH2:15][N:11]4[N:10]=3)[CH:17]=2)=[CH:34][CH:35]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 698614-Tert-ButylanilineHCID 674246843-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride

Product 1

HCID 46701906N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride (45 mg, 0.125 mmol) was dissolved in thionylchloride (1 mL) and stirred at 60° C. for 1 hour. The solvent was distilled and the residue was taken up with toluene, evaporated to dryness and dried under high vacuum for 1 h. The acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen and 4-tert-butylaniline (0.030 mL, 0.187 mmol, 1.5 eq) was added. The mixture was stirred at room temperature for 1 h and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5 to give 44 mg of N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide as a white solid (77%).

Workup

  1. distillationThe solvent was distilled
  2. customevaporated to dryness
  3. customdried under high vacuum for 1 h
  4. dissolutionThe acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen
  5. stirringThe mixture was stirred at room temperature for 1 h
  6. washwashed with saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5

Sources & evidence

ORD record
ord-60819d40753b43e4ad7a8990ed0dc1c1
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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