HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → ((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate | HCID 67111989 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | ((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol | HCID 44599523 | — |
Reaction Steps
(2S,4S)-tert-butyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.084 g, 0.154 mmol) in 2 mL DCM was added trifluoroacetic acid (0.200 mL) After 3 d, the reaction mixture was concentrated, dissolved in DMSO, filtered, and purified by RPHPLC, gradient, 10-100% ACN/TFA in H2O/TFA. Product-containing fractions were concentrated in vacuo to give ((2S,4S)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidin-2-yl)methanol. MS (ESI) m/z: Calculated: 445.2; Observed: 445.8 (M++1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07842685B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-db4e5e03f2584f5e822d21ecaeef1bd4 |
| Source note | uspto-grants-2010_11 |