Diethyl chloromalonate → Ethyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

HRID 2282174Notes

Reaction equation

C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[C:21]([C:22]2[S:23]C(C3NC=NN=3)=C(C3C=CC=CC=3)[N:26]=2)=[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1.Cl[CH:39]([C:45]([O:47]CC)=O)[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CC(O)C>[OH:47][C:45]1[N:26]=[C:22]([C:21]2[C:13]([CH3:12])=[N:14][N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=23)[S:23][C:39]=1[C:40]([O:42][CH2:43][CH3:44])=[O:41]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (1.7 g, 7.5 mmol) produced in Example 11-B (v) and diethyl chloromalonate (2.0 g, 11 mmol) in 2-propanol (25 mL) was stirred at 90° C. for 4 hr with heating. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration and dried to give ethyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (1.45 g, 64%) as a yellow solid.

Workup

temperaturewith heating
temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitated solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-0456d43e5b1146279fea8666a8b302d5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139589B2

Reaction notes

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