Synthesis of cerdulatinib
AssigneePortola Pharmaceuticals, Inc.
InventorsAnjali Pandey, Arvinder Sran, Ying Chen, Daniele Poggiali, Tiziano Fumagalli
Life of this patent
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Abstract
The present disclosure provides processes for the preparation of cerdulatinib, which is of formula I: or a salt thereof. The disclosure also provides intermediates and processes for the preparation of the intermediates useful in the preparation of cerdulatinib or a salt thereof.
Claims41
A process for preparing cerdulatinib, which is of formula I:
- or a salt thereof, wherein the process comprises contacting Compound A or a salt thereof with Compound B or a salt thereof under conditions to form cerdulatinib or a salt thereof:
- wherein Compound A is Compound A-2 or Compound A-3 or a salt thereof, or a mixture thereof,
- wherein Compound A-2 or Compound A-3 or a salt thereof, or a mixture thereof, is prepared by a method comprising contacting an oxidizing agent with Compound C:
- or a salt thereof;
- wherein Compound C is prepared by a method comprising contacting Compound D-1
- or a salt thereof with formamide and sodium ethoxide.
A three-step, one-pot process for preparing cerdulatinib or a salt thereof, comprising steps (1) contacting Compound F
- or a salt thereof with ammonia or a salt thereof to form Compound E
- or a salt thereof,
- (2) contacting Compound E or a salt thereof with cyclopropylamine or a salt thereof to form Compound A
- or a salt thereof, and
- (3) contacting Compound A or a salt thereof with Compound B
- or a salt thereof to form cerdulatinib or a salt thereof, wherein X is selected from the group consisting of Cl, Br, CH3S(O)— and CH3S(O)2—, X1 and X2 are independently a leaving group, and wherein all of steps (1)-(3) are conducted in one reactor without isolation of intermediates.
A three-step, one-pot process for preparing cerdulatinib or a salt thereof, comprising steps (1) contacting Compound F-1
- or a salt thereof with ammonia or a salt thereof to form Compound E-1
- or a salt thereof,
- (2) contacting Compound E-1 or a salt thereof with cyclopropylamine or a salt thereof to form Compound A-1:
- or a salt thereof, and
- (3) contacting Compound A-1 or a salt thereof with Compound B:
- or a salt thereof to form cerdulatinib or a salt thereof, wherein all of steps (1)-(3) are conducted in one reactor without isolation of intermediates.
A compound of Formula A:
- or a salt thereof, wherein X is Cl or Br.
A compound
- or a salt thereof.
A process for preparing cerdulatinib, which is of formula I:
- or a salt thereof, wherein the process comprises contacting Compound A or a salt thereof with Compound B or a salt thereof under conditions to form cerdulatinib or a salt thereof:
- wherein Compound A is Compound A-2 or Compound A-3 or a salt thereof, or a mixture thereof,
- wherein Compound A-2 or Compound A-3 or a salt thereof, or a mixture thereof, is prepared by a method comprising contacting an oxidizing agent with Compound C:
- or a salt thereof;
- wherein Compound C is prepared by a method comprising contacting Compound D-2
- or a salt thereof with formamide.
Dependencies are inferred from the claim text.