(R)-dimethyl 2-aminopentanedioate → HCID 72547683, compound

HRID 2206421Notes

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.[NH2:43][C@H:44]([CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])[C:45]([O:47][CH3:48])=[O:46]>>[ClH:1].[CH3:48][O:47][C:45](=[O:46])[C@H:44]([NH:43][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][C:31]([NH:30][C:28]([C@H:9]2[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:42])[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]([CH3:26])([CH3:27])[CH3:25])[NH:10]2)=[O:29])=[C:32]([O:40][CH3:41])[CH:33]=1)[CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52]

Participants

Reactant 2

HCID 7019516(R)-dimethyl 2-aminopentanedioate

HCID 53358942Idasanutlin

Product 1

HCID 72547683HCID 72547683, 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 (R)-dimethyl 2-aminopentanedioate to give (R)-2-(4-{[(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-carbonyl]-amino}-3-methoxy-benzoylamino)-pentanedioic acid dimethyl ester, hydrochloride. MS (ES+) m/z calcd. for C38H41Cl2F2N4O7: [(M+H)+]773. found: 773.

Sources & evidence

ORD record: ord-c739612cef164ba0b6a1bed026564e51
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371280B2

Reaction notes

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