Curate this paper into an ORD dataset

Build an Open Reaction Database (ORD) dataset of the reactions reported in:

• Paper: Benchtop 19F NMR Spectroscopy optimized Knorr pyrazole synthesis of Celecoxib and Mavacoxib, 3-(trifluoromethyl) pyrazolyl benzenesulfonamides Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)
• Authors: Andrew Chyu, Selina Xi, Joshua Kim et al.
• Published: Spectroscopy J, 2024-11-11
• DOI: 10.3390/spectroscj2040014
• ORD wishlist card: open on GitHub

The reference input card holds these facts, the source-data locations and the notes below in machine-readable form.

Scope

Every reaction the paper reports with its data (the wishlist estimates about 100 reactions; kinetics): inputs with amounts and roles, conditions, workups, outcomes and provenance, following the ord-curation Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.

Source data

Source: Spectroscopy Journal 2024, 10.3390/spectroscj2040014 (CC BY 4.0 article; preprint on ChemRxiv). This is Knorr pyrazole synthesis toward celecoxib and mavacoxib, monitored by benchtop 19F NMR: about 100 kinetic profiles. The SI shows the kinetic data only as chart images, so the underlying time-course data must be obtained from the authors (coordinate through ORD). Once raw data is available, each profile maps to an ORD reaction with time-resolved outcomes. The structures are simple and known (1,3-dicarbonyl plus aryl hydrazine), so SMILES generation is easy.

Known locations:

• https://doi.org/10.3390/spectroscj2040014: Spectroscopy Journal (MDPI) 2024 article and SI, where the kinetics appear only as charts. The MDPI page returned 403 to the automated request, so it was not inspected. (license: CC-BY-4.0 (article, per Crossref))
• https://chemrxiv.org/engage/chemrxiv/article-details/66fb91cb12ff75c3a10579c9: ChemRxiv preprint. Not fetched because ChemRxiv sits behind a Cloudflare challenge. (license: unknown)

Pitfalls

Kinetic time-course data needs a time-series outcome representation (multiple outcomes at different reaction times) and NMR-derived conversion or yield. Only charts are public. Values digitized from plots would be low-fidelity and hard to verify. Regioisomer formation may need separate product entries.

Deliver

• dataset: the ORD Dataset, compressed (.binpb.gz, .pb.gz, .txtpb.gz, .pbtxt.gz or .parquet), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.
• sources: a .zip with a README.md (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and validation.txt, the output of ORD's validator (ord-schema 0.8.3) on the dataset file.

Before you start

Open the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.