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US 10,329,288 B2Granted
Process for preparing a compound
AssigneesGenentech, Inc., Array BioPharma Inc.
InventorsChong Han, Keena Green, Francis Gosselin, Michelangelo Scalone, Paul J. Nichols, Weidong Liu, Keith L. Spencer, Zackary D. Crane, Peter J. Stengel, Sagar Shakya
Life of this patent
Estimating the term…
Abstract
The invention provides processes of preparation thereof useful in the preparation of compounds that can be used as CHK1 inhibitors.
Claims20
A process for preparing (R)-5-bromo-4-(3-amino)piperidin-1-yl)-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridine of Formula (I):
- or a pharmaceutically acceptable salt thereof, comprising the step of reacting a compound of Formula (II):
- wherein X is I, Cl, or Br, with a compound of Formula (III):
- wherein R is an amino protecting group selected from the group consisting of:
- triphenylmethyl (trityl), tert-butyloxycarbonyl (Boc), carboxybenzyl (Cbz), trifluoroacetyl and acetyl,
- to provide a compound of Formula (IV):
- subjecting a compound of Formula (IV) to a nitro reduction to obtain a compound of Formula (V):
- reacting a compound of Formula (V) with a compound of Formula (VI):
- wherein Rl is selected from the group consisting of chlorine, fluorine, bromine, and OR2,
- wherein R2 is selected from the group consisting of cyclopropylcarbonyl, isobutylcarbonyl, isopropylcarbonyl, ethylcarbonyl, methylcarbonyl, 2-pyridyl, and N-succinimidyl, to obtain a compound of Formula (VII):
- removing the protecting group R in the compound of Formula (VII) to provide the compound of Formula (I), or a pharmaceutically acceptable salt thereof.
7 more elements
A process for preparing a compound of Formula (IV) or a salt thereof:
- wherein R is an amino protecting group selected from the group consisting of:
- triphenylmethyl (trityl), tert-butyloxycarbonyl (Boc), carboxybenzyl (Cbz), trifluoroacetyl and acetyl, comprising reacting a compound of Formula (II):
- wherein X is wherein X is I, Cl, or Br, with a compound of Formula (III):
- to provide the compound of Formula (IV) or a salt thereof.
1 more element
Dependencies are inferred from the claim text.