Curate this paper into an ORD dataset

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

• Paper: Leveraging High-Throughput Experimentation to Drive Pharmaceutical Route Invention: A Four-Step Commercial Synthesis of Branebrutinib (BMS-986195)
• Authors: Jason M. Stevens, Eric M. Simmons, Yichen Tan et al.
• Published: OPRD, 2022-02-15
• DOI: 10.1021/acs.oprd.1c00443
• 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: 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: Stevens et al., Org. Process Res. Dev. 2022, 26, 1174 (doi:10.1021/acs.oprd.1c00443). Describes invention of a four-step commercial route to branebrutinib (BMS-986195), using parallel HTE across the proposed steps, including a novel indolization. The article is closed-access, and no supporting-information files were found. HTE results are expected to appear only as figures or heatmaps in the article. Plate-level numeric data would have to be released by the authors, and this has not been confirmed.

Known locations:

• https://pubs.acs.org/doi/10.1021/acs.oprd.1c00443: OPRD 2022, 26, 1174-1183 article page (closed access). HTE-driven four-step route to branebrutinib including an indolization step. No SI listing seen. (license: ACS standard (closed))
• https://api.figshare.com/v2/articles/search: figshare search for ACS SI DOIs 10.1021/acs.oprd.1c00443.s001-s003 and title: no results (license: n/a)

Pitfalls

Multiple HTE screens across different steps/reaction types, so likely several datasets. Heatmap-derived outcomes are approximate (assay yield / LCAP). Some screening components may be named only generically (ligand/catalyst kits). Process-scale results would be separate records.

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.