1-(2-Hydroxyethyl)-4-methylpiperazine → HCID 72549331, compound

HRID 2206395Notes

Reaction equation

HRID 2206395 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]([OH:37])=[O:36])=[CH:33][C:32]=2[O:40][CH3:41])=[O:29])[CH:5]=[CH:6][CH:7]=1.[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51]O)[CH2:46][CH2:45]1>>[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][O:36][C:35](=[O:37])[C:34]2[CH:38]=[CH:39][C:31]([NH:30][C:28]([C@H:9]3[C@H:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=4[F:42])[C@:12]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])[NH:10]3)=[O:29])=[C:32]([O:40][CH3:41])[CH:33]=2)[CH2:46][CH2:45]1

Participants

3

Reactant 2

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 53358942Idasanutlin

Product 1

HCID 72549331HCID 72549331, 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 2-(4-methylpiperazin-1-yl)ethanol to give 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-benzoic acid 2-(4-methyl-piperazin-1-yl)-ethyl ester. MS (ES+) m/z calcd. for C38H44Cl2F2N5O4: [(M+H)+]: 742. found: 742.

Sources & evidence

ORD record
ord-a941f8cfc3ef4c40bb48ca823809694d
Source dataset
uspto-grants-2016_06
Patent number
US09371280B2

Reaction notes

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