HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1426908Generated: November 2, 2026
3-Amino-1-propanol → (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
https://huagongshe.com/reaction/1426908
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Amino-1-propanol | HCID 9086 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 66847769 | HCID 66847769 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide | HCID 67471053 | 69% |
Reaction Steps
To a DMF (2 mL) suspension of (R)-5-(2-(5-fluoro-2-methoxy pyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation B, 250 mg, 0.700 mmol) and HATU (319 mg, 0.840 mmol) cooled to 0° C. was added 3-aminopropan-1-ol (0.0642 mL, 0.840 mmol) drop-wise, resulting in a clear yellowish solution. After dropwise addition of DIEA (0.366 mL, 2.10 mmol), ice bath was removed and reaction was stirred at ambient temperature for 1 hour. The reaction was directly purified on reverse phase column chromatography (Biotage SP4 system, C-18 25+M column, 0 to 54% Acetonitrile/water), to provide the product as white solid (200 mg, 69% yield). MS (apci) m/z=415.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933084B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-ea4722f074224389b6c6c8808767f49a |
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| Source note | uspto-grants-2015_01 |
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