HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → n-{(3r,4s)-1-[(3-Chloro-7-oxo-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}-3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazine-6-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| 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-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid | HCID 21873787 | — |
| Reactant | racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one | HCID 68685696 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | n-{(3r,4s)-1-[(3-Chloro-7-oxo-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}-3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazine-6-carboxamide | HCID 24871917 | 59% |
Reaction Steps
The free base of the title compound was synthesised from racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (79 mg), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (for a synthesis see WO2003087098, Example 301(b)) (50 mg), triethylamine (0.066 ml) and HATU (95 mg) in DMF (2 ml) according to the general method of Example 9 in 59% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07732461B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-f72d5f9f6cf8417da55a79919becba0b |
| Source note | uspto-grants-2010_06 |