HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → (S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-1,3-thiazole-4-carboxylic acid | HCID 2763209 | — |
| 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 | (S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate | HCID 59332360 | — |
| Product | (S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate | HCID 58182192 | — |
Reaction Steps
To a mixture of (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate (1.04 g, 5.00 mmol) and 2-bromothiazole-4-carboxylic acid (1.46 g, 5.00 mmol) in Methylene chloride (10 mL, 200 mmol) was added N,N-Diisopropylethylamine (3.48 mL, 20.0 mmol) and N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (2.28 g, 6.00 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then concentrated and the residue was purified on silica eluting with 0 to 5% MeOH in DCM with 1% NH4OH (2.41 g, 99.9%). ESIMS m/z=484.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08435976B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-2e4d972975d04f16a3fbd5c04a99d45d |
| Source note | uspto-grants-2013_05 |