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US 2023/0219922 A1Published application
Process for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde
AssigneeGlobal Blood Therapeutics, Inc.
InventorsZhe Li, Nathan Guz, Yiyang Shao, Julieana Cocuz, Markus Frieser, George Petros Yiannikouros, Liang Liao
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Abstract
Disclosed herein are processes for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde (also referred to herein as Compound (I)) and intermediates used in such processes. Compound (I) binds to hemoglobin and increases its oxygen affinity and hence can be useful for the treatment of diseases such as sickle cell disease.
Claims37
A process of synthesizing Compound (I):
- the process comprising:
- Step (i):
- treating a compound of formula (2):
- wherein each R is —CH(CH2R1)—OR2 or tetrahydropyran-2-yl optionally substituted with one, two, or three alkyl;
- and wherein R1 is hydrogen or alkyl, and R2 is alkyl;
- with an acid to provide compound (1):
- Step (ii):
- reacting compound (1) with a compound of formula (3):
- wherein LG is a leaving group under alkylation reacting conditions to provide Compound (I);
- and
- Step (iii):
- optionally crystallizing Compound (I) from Step (ii) from heptane and methyl tert-butyl ether at 45°+/−5° C. to 55°+/−5° C.
9 more elements
An intermediate of formula (2):
- wherein each R is —CH(CH2R1)OR2;
- and
- wherein R1 is hydrogen or alkyl, and R2 is alkyl.
Dependencies are inferred from the claim text.