HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylimidazole → Methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylimidazole | HCID 1390 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Methyl p-aminosalicylate | HCID 77787 | — |
| Reactant | 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid | HCID 68379514 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-hydroxybenzoate | HCID 68379217 | 102.5% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921383B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-719be4983bbd47179142aed0e0d454ad |
| Source note | uspto-grants-2014_12 |