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US 2001/0011142 A1Published application
Processes and intermediates useful to make antifolates
AssigneeEli Lilly and Company
InventorDouglas Patton Kjell
Life of this patent
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Abstract
The present application relates to a series of novel sulfonic acid metal cation salts of the formula 1 which are useful intermediates to prepare antifolate 5-substituted pyrrolo[2,3-d]pyrimidines. The present invention also relates to a novel process for preparing the sulfonic acid metal cation salts and to a novel process for preparing aldehydes of the formula 2 from the corresponding sulfonic acid metal cation salts.
Claims26
A compound of formula IV:
- 15
- wherein:
- M is a metal cation;
- n is 1 or 2;
- R2 is NHCH (CO2R3)CH2CH2CO2R3 or OR3;
- R3 is independently at each occurrence a carboxy protecting group;
- and
- X is a bond or C1-C4 alk-diyl.
5 more elements
A process for preparing a compound of formula III:
- 16
- wherein:
- R2 is NHCH (CO2R3)CH2CH2CO2R3 or OR3;
- R3 is independently at each occurrence a carboxy protecting group;
- X is a bond or C1-C4 alk-diyl;
- comprising:
- reacting a compound of formula IV:
- 17
- wherein:
- X and R2 are defined above for formula III;
- M is a metal cation;
- and
- n is 1 or 2;
- with a trialkylsilyl halide in a solvent.
11 more elements
A process for preparing a compound of formula IV:
- 18
- wherein:
- M is a metal cation;
- n is 1 or 2;
- R2 is NHCH(CO2R3)CH2CH2CO2R3 or OR3;
- R3 is independently at each occurrence a carboxy protecting group;
- X is a bond or C1-C4 alk-diyl;
- comprising:
- reacting a compound of formula III:
- 19
- wherein:
- R2 and X are as defined above for formula IV;
- with a compound of the formula M(HSO3−)n:
- wherein:
- M is defined above for formula IV;
- and
- n is 1 or 2;
- in a solvent.
15 more elements
Dependencies are inferred from the claim text.