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

HRID 2282180Notes

Reaction equation

HRID 2282180 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]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC(O)C>[CH:24]1([C:22]2[N:13]=[C:12]([C:11]3[C:3]([CH3:2])=[N:4][N:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=34)[S:14][C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochlorideHCID 86649589Ethyl 2-chloro-3-cyclohexyl-3-oxopropanoate

Product 1

HCID 66855471Ethyl 4-cyclohexyl-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylateYield 94.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (300 mg, 1.3 mmol) produced in Example 11(v), ethyl 2-chloro-3-cyclohexyl-3-oxopropanoate (870 mg, 3.7 mmol) produced above and 2-propanol (50 mL) as starting materials and in the same manner as in Example 11-B (vi), the title compound (455 mg, 74%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-828dea74fd09464d89135ca5644f1e82
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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