2-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride → Ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-[2-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate

HRID 2282189Notes

Reaction equation

HRID 2282189 reaction equation
Cl.[CH3:2][C:3]1[C:11]([C:12](=[S:14])[NH2:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.Cl[CH:16]([C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC(O)C>[CH3:2][C:3]1[C:11]([C:12]2[S:14][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:30])([F:31])[F:32])[N:13]=2)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1

Participants

4

Reactant 2

HCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochlorideHCID 86649590Ethyl 2-chloro-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate

Product 1

HCID 66855669Ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-[2-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (100 mg, 0.44 mmol) produced in Example 11-B(v), ethyl 2-chloro-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate (250 mg, 0.85 mmol) produced above and 2-propanol (25 mL) as starting materials and in the same manner as in Example 11-B(vi), the title compound (158 mg, 84%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-0e6f793b87bb4fd2aa826f908b3e0353
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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