HCID 11665674, compound → HCID 72547689, compound

HRID 2206423Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:42])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][C:32]=2[O:40][CH3:41])=[O:29])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:44][C@@H:45]1[C@@H:50]([OH:51])[C@H:49]([OH:52])[C@@H:48]([CH2:53][OH:54])[O:47][C@@H:46]1[OH:55]>>[ClH:1].[CH3:41][O:40][C:32]1[CH:33]=[C:34]([C:35](=[O:36])[NH:44][C@@H:45]2[C@@H:50]([OH:51])[C@H:49]([OH:52])[C@@H:48]([CH2:53][OH:54])[O:47][C@@H:46]2[OH:55])[CH:38]=[CH:39][C:31]=1[NH:30][C:28]([C@H:9]1[C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:42])[C@:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])[NH:10]1)=[O:29]

Participants

Reactant 2

HCID 11665674HCID 11665674, compound

HCID 53358942Idasanutlin

Product 1

HCID 72547689HCID 72547689, compound

Procedure

In a manner similar to the method described in Example 14, 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid (prepared as described in US20100152190A1) was reacted with (2S,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride to give (2R,3S,4R,5S)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [2-methoxy-4-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl)-phenyl]-amide, hydrochloride. MS (ES+) m/z calcd. for C37H41Cl2F2N4O8: [(M+H)+]777. found: 777.

Sources & evidence

ORD record: ord-f8a05d2c640f481aab14ac409b5238b3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371280B2

Reaction notes

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