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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1410083Generated: October 26, 2026

1-Methylimidazole → Methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate

https://huagongshe.com/reaction/1410083

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylimidazoleHCID 1390—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
ReactantMethyl p-aminosalicylateHCID 77787—
Reactant1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acidHCID 68379514—
SolventDichloromethaneHCID 6344—
ProductMethyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoateHCID 68379217102.5%

Reaction Steps

To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (80 mg, 0.19 mmol) and methyl 4-amino-2-hydroxybenzoate (32 mg, 0.19 mmol) in dichloromethane (15 mL) were added the solution of 1-methyl-1H-imidazole (63 mg, 0.76 mmol) and EDCI (147 mg, 0.76 mmol) in dichloromethane (5 mL), the reaction mixture was stirred at room temperature for 24 hours, the solvent was removed in vacuo, methanol (5 mL) was added, the precipitate was collected by filtration to afford methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate (110 mg, crude) which was used directly in the next step without further purification. LC-MS: tR=565 [M+H]+, 1.64 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921383B2
Source datasetuspto-grants-2014_12
ORD IDord-719be4983bbd47179142aed0e0d454ad
Source noteuspto-grants-2014_12