HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 3,3-Dimethyl-1-(oxetan-3-yl)piperazine | HCID 67492262 | — |
| Reactant | 5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid | HCID 86648236 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(2,2-dimethyl-4-oxetan-3-ylpiperazin-1-yl)methanone | HCID 59606073 | — |
Reaction Steps
A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid (100 mg, 0.33 mmol), 3,3-dimethyl-1-oxetan-3-ylpiperazine (62 mg, 0.36 mmol), HATU (278 mg, 0.37 mmol) and DIPEA (65 μL, 0.37 mmol) in DCM (3 mL) was allowed to stir at r.t. for 18 h. The reaction mixture was concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-2%) affording the title compound as a yellow solid. LCMS (method H): RT 2.67 min, [M+H]+ 453.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173650B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-4689b8d2214545a6a52847b5cc6b4095 |
| Source note | uspto-grants-2012_05 |