p-Toluenesulfonic acid monohydrate → HCID 178427648, compound

HRID 2282170Notes

Reaction equation

HRID 2282170 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:22]3[NH:26][CH:25]=[N:24][N:23]=3)=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(O)C>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:22]3[NH:26][CH:25]=[N:24][N:23]=3)=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178433737HCID 178433737, compound

Product 1

HCID 178427648HCID 178427648, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-phenyl-1,3-thiazole-5-carboxamide (200 mg, 0.6 mmol) produced above and N,N-dimethylformamide dimethyl acetal (5 mL) was stirred at 100° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, hydrazine monohydrate (0.29 mL, 6.0 mmol) and acetic acid (10 mL) were added to the obtained residue, and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and aqueous sodium bicarbonate solution and diethyl ether were added to the obtained residue. The resulting precipitate was collected by filtration, washed with water and diethyl ether and dried to give 2-methyl-3-[4-phenyl-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridine (210 mg, 98%) as a pale-yellow solid. The obtained 2-methyl-3-[4-phenyl-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridine (90 mg, 0.25 mmol) and p-toluenesulfonic acid monohydrate (57 mg, 0.3 mmol) were dissolved in ethanol (6 mL) by heating, and the mixture was concentrated under reduced pressure. The obtained residue was crystallized from ethanol and ethyl acetate to give the title compound (93 mg, 70%) as a pale-orange solid.

Workup

  1. temperatureby heating
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe obtained residue was crystallized from ethanol and ethyl acetate

Sources & evidence

ORD record
ord-7356b781682d4aedb378101683485d9d
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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