2-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride → ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole-5-carboxylate

HRID 2282191Notes

Reaction equation

HRID 2282191 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)[CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[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]([CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[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 86649591ethyl 2-chloro-3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate

Product 1

HCID 66855571ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole-5-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (400 mg, 1.8 mmol) produced in Example 11-B(v), ethyl 2-chloro-3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (1.0 g, 4.3 mmol) produced above and 2-propanol (40 mL) as starting materials and in the same manner as in Example 11-B(vi), the title compound (530 mg, 81%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-a946c056a86a407b85ee95676434cb5b
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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