52756-23-7 → HCID 59159243, compound

HRID 1096278Notes

Reaction equation

ClC1C=C(NC(C)C(O)=O)C=CC=1F.COC(OC)CNCCCN1CCC2(CC2)[C@H](O)C1.[Cl:34][C:35]1[CH:36]=[C:37]([NH:42][CH:43]([CH3:65])[C:44]([N:46]([CH2:59][CH:60](OC)OC)[CH2:47][CH2:48][CH2:49][N:50]2[CH2:57][CH2:56][C:53]3([CH2:55][CH2:54]3)[C@H:52]([OH:58])[CH2:51]2)=[O:45])[CH:38]=[CH:39][C:40]=1[F:41]>>[Cl:34][C:35]1[CH:36]=[C:37]([N:42]2[CH2:60][CH2:59][N:46]([CH2:47][CH2:48][CH2:49][N:50]3[CH2:57][CH2:56][C:53]4([CH2:54][CH2:55]4)[C@H:52]([OH:58])[CH2:51]3)[C:44](=[O:45])[C@@H:43]2[CH3:65])[CH:38]=[CH:39][C:40]=1[F:41]

Participants

Reactant 3

HCID 277193652756-23-72×

HCID 66783273HCID 66783273, compound

HCID 66783309HCID 66783309, compound

Product 1

HCID 59159243HCID 59159243, compound

Procedure

The title compound was produced in analogy with examples 74 and 75, steps D-F. Thus, coupling of 2-(3-chloro-4-fluoro-phenylamino)-propionic acid (intermediate 14) with (S)-6-[3-(2,2-dimethoxy-ethylamino)-propyl]-6-aza-spiro[2.5]octan-4-ol (examples 74/75C) in step D led to 2-(3-chloro-4-fluoro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-propionamide, which was cyclized in step E. Finally, HPLC purification of the epimeric mixture, 4-(3-chloro-4-fluoro-phenyl)-1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-3-methyl-piperazin-2-one, in step F afforded the title compound. Light yellow gum, MS: 410.2 (M+H)+.

Workup

customFinally, HPLC purification of the epimeric mixture, 4-(3-chloro-4-fluoro-phenyl)-1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-3-methyl-piperazin-2-one

Sources & evidence

ORD record: ord-bc578d61313d4f619fd73afca3306619
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138175B2

Reaction notes

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