PATENT CLAIM ANALYSIS

Application Number: 16011178
Application Type: Utility
Filing Date: 2018-06
Publication Date: 2018-12
Patent Classification: ["548", "262200"]

Abstract:
Described herein is the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules. A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.

Claim (Index 11):
A method to prepare an urazole compound of Formula I: or the enantiomer thereof;\n wherein\n R 1  is alkyl, alkenyl, aryl, or heteroaryl; \n R 2 , R 3  and R 6  are each independently H, D, halo, alkyl, cycloalkyl, OR A , N(R A ) 2 , aryl, heteroaryl, or R 2  and R 3  taken together form a ring wherein the ring is unsaturated or aromatic; \n R 4  and R 5  are each independently H, alkyl, cycloalkyl, or aryl; \n each R A  is independently H, alkyl, cycloalkyl, C(\u2550O)R B , aryl, or heteroaryl; \n each R B  is independently H, OH, halo, alkyl, aryl, heteroaryl, or N(R A ) 2 , wherein N(R A ) 2  is not recursive with C(\u2550O)R B ; and \n m is 0, 1, or 2; \n \n wherein each alkyl, cycloalkyl, alkenyl, aryl, and heteroaryl is optionally substituted with one or more substituents; \n comprising:\n a) irradiating a mixture of an aromatic substrate and a compound of Formula X: \n \n wherein R 4  is H, alkyl, cycloalkyl, or aryl; b) contacting the mixture with a transition metal catalyst and an organometallic nucleophile; and c) quenching the mixture; thereby forming the dearomatized trans-1,2-carboaminated compound of Formula I by cycloaddition and transition metal catalyzed dearomative carboamination of an aromatic substrate.

Metadata:
- Claim Count in Document: 38.0
- Percentile: 94.0
- Lexical Diversity: 1.45545
- Patent Class: 548.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: False
- Related Applications: ['14065815', '10586287', '15109396', '15219710', '15375716']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7261619187337547
- 35 USC 102 Novelty (BERT): 0.5020493419811476
- Combined Prediction Score: 0.703750661058494
- Mean Citation Score: 262.02361800000006
- Max Citation Score: 270.36926
- Similarity Product: 200.29965831817032

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test