The PMI Predictor app to enable green-by-design chemical synthesis

Borovika, Alina; Albrecht, Jacob; Li, Jun; Wells, Andrew S.; Briddell, Christiana; Dillon, Barry R.; Diorazio, Louis J.; Gage, James R.; Gallou, Fabrice; Koenig, Stefan G.; Kopach, Michael E.; Leahy, David K.; Martinez, Isamir; Olbrich, Martin; Piper, Jared L.; Roschangar, Frank; Sherer, Edward C.; Eastgate, Martin D.

doi:10.1038/s41893-019-0400-5

Cited by 47 publications

(35 citation statements)

References 35 publications

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“…Moreover, it should be noted that aqueous waste contaminated with organic material should be disposed of as organic waste (water should be treated as organic waste in PMI calculations). 103…”

Section: Water-based Sppsmentioning

confidence: 99%

Greening the synthesis of peptide therapeutics: an industrial perspective

et al. 2020

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Section: Water-based Sppsmentioning

confidence: 99%

Greening the synthesis of peptide therapeutics: an industrial perspective

et al. 2020

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“…For the sake of comparison and to have a better idea on how far the process can be optimized in term of waste generation, we used the recently developed PMI prediction tool by Borovika et al accessible online (Figures 6 and 7). [36][37][38] The estimated cPMI range has a mean of 128 (see Supporting Information for details) with a 95% confidence interval. This is obviously below the value of 344 calculated with real data from the process.…”

Section: Environmental Impact Evaluationmentioning

confidence: 99%

Optimized Synthesis of 7-Azaindazole by a Diels–Alder Cascade and Associated Process Safety

Brach

Fouler

Bizet

et al. 2020

Org. Process Res. Dev.

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Although pyrimidines are not among the most reactive partners in intramolecular inverse-electron demand [4ps+2ps] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels-Alder cascade that starts from a pyrimidine substituted in the 2-position by an (alkynyl)hydrazone. The safety of the process and the environmental impact were thoroughly evaluated. Eventually, a selection of crosscoupling reactions of 17 was studied and allowed the introduction of carbon-and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

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“…. [33][34][35] The estimated cPMI range has a mean of 128 (see Supporting Information for details) with a 95% confidence interval. This is obviously below the value of 344 calculated with real data from the process.…”

Section: Online (Figures 6 and 7)mentioning

confidence: 99%

Optimized Synthesis of 7-Aza-Indazoles by Diels–Alder Cascade and Associated Process Safety

Brach¹,

Fouler²,

Bizet³

et al. 2020

Preprint

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Although pyrimidines are not among the most reac-tive partners in intramolecular inverse-electron de-mand [4πs+2πs] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels–Alder cascade that starts from a pyrimidine substituted in the 2-position by an (alkynyl)hydrazone. The safety of the process was carefully studied by DSC studies. Eventually, a selection of cross-coupling reactions of 17 was studied and allowed the introduction of carbon- and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

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The PMI Predictor app to enable green-by-design chemical synthesis

Cited by 47 publications

References 35 publications

Greening the synthesis of peptide therapeutics: an industrial perspective

Greening the synthesis of peptide therapeutics: an industrial perspective

Optimized Synthesis of 7-Azaindazole by a Diels–Alder Cascade and Associated Process Safety

Optimized Synthesis of 7-Aza-Indazoles by Diels–Alder Cascade and Associated Process Safety

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