HCID 61722216, compound → HCID 59159279, compound

HRID 1096277Notes

Reaction equation

HRID 1096277 reaction equation
FC1C=CC(NC(C)C(O)=O)=CC=1C(F)(F)F.COC(OC)CNCCCN1CCC2(CC2)[C@H](O)C1.[F:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][CH:45]([CH3:67])[C:46]([N:48]([CH2:61][CH:62](OC)OC)[CH2:49][CH2:50][CH2:51][N:52]2[CH2:59][CH2:58][C:55]3([CH2:57][CH2:56]3)[C@H:54]([OH:60])[CH2:53]2)=[O:47])=[CH:40][C:39]=1[C:68]([F:71])([F:70])[F:69]>>[F:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH2:62][CH2:61][N:48]([CH2:49][CH2:50][CH2:51][N:52]3[CH2:59][CH2:58][C:55]4([CH2:57][CH2:56]4)[C@H:54]([OH:60])[CH2:53]3)[C:46](=[O:47])[C@@H:45]2[CH3:67])=[CH:40][C:39]=1[C:68]([F:70])([F:69])[F:71]

Participants

4

Reactant 3

HCID 61722216HCID 61722216, compound2×HCID 66783156HCID 66783156, compoundHCID 66783309HCID 66783309, compound

Product 1

HCID 59159279HCID 59159279, compound

Procedure

The title compound was produced in analogy with examples 74 and 75, steps D-F. Thus, coupling of 2-(4-fluoro-3-trifluoromethyl-phenylamino)-propionic acid (intermediate 13) 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-(4-fluoro-3-trifluoromethyl-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-(4-fluoro-3-trifluoromethyl-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: 444.3 (M+H)+.

Workup

  1. customFinally, HPLC purification of the epimeric mixture, 4-(4-fluoro-3-trifluoromethyl-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-68c1d024707d466092479d952834763a
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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