Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | 2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine | HCID 58065603 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Vericiguat | HCID 54674461 | — |
Reaction Steps
31.75 g (86.20 mmol) of the compound from example 30A were initially charged in pyridine (600 ml) under argon and cooled to 0° C. Then a solution of 6.66 ml (86.20 mmol) of methyl chloroformate in dichloromethane (10 ml) was added dropwise and the mixture was stirred at 0° C. for 1 h. Thereafter, the reaction mixture was brought to RT, concentrated under reduced pressure and co-distilled repeatedly with toluene. The residue was stirred with water/ethanol and then filtered off with suction using a frit, and subsequently washed with ethanol and ethyl acetate. Subsequently, the residue was stirred again with diethyl ether, filtered off with suction and then dried under high vacuum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09096592B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-fe85ecb170c04e6d92a8c97deaa2e1ca |
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| Source note | uspto-grants-2015_08 |
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