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

HRID 1530010Notes

Reaction equation

HRID 1530010 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:21](OC)=[O:22])[C:17]([O:19][CH3:20])=[O:18]>CC(O)C>[OH:22][C:21]1[N:13]=[C:12]([C:11]2[C:3]([CH3:2])=[N:4][N:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=23)[S:14][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 120070Dimethyl chloromalonateHCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride

Product 1

HCID 136376955Methyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylateYield 82.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (3.0 g, 13 mmol) produced in Example 11-B (v) and dimethyl chloromalonate (6.6 g, 40 mmol) in 2-propanol (40 mL) was stirred at 90° C. for 7 hr. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration, washed with ethyl acetate and diisopropyl ether and dried to give the title compound (3.1 g, 82%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with ethyl acetate and diisopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-fe4a4840d9e34f86be7361dcf38f92f5
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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