HCID 86636977, compound → HCID 86636976, compound

HRID 1366526Notes

Reaction equation

HRID 1366526 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:32]2[CH2:38][CH:37]([N:39]([CH3:41])[CH3:40])[C:34]3([CH2:36][CH2:35]3)[CH2:33]2)[C:5]([F:31])=[C:6]([NH:8][NH:9][C:10](=[O:30])[C@H:11]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:12][N:13]([O:16]CC2C=CC=CC=2)[CH:14]=[O:15])[CH:7]=1>CO.[Rh]>[Cl:1][C:2]1[CH:3]=[C:4]([N:32]2[CH2:38][CH:37]([N:39]([CH3:41])[CH3:40])[C:34]3([CH2:36][CH2:35]3)[CH2:33]2)[C:5]([F:31])=[C:6]([NH:8][NH:9][C:10](=[O:30])[C@H:11]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[CH:7]=1

Participants

4

Reactant 1

HCID 86636977HCID 86636977, compound

Product 1

HCID 86636976HCID 86636976, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

[(2R)-3-(2-{5-Chloro-3-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-fluorophenyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (300 mg, 0.51 mmol) was dissolved in 5 mL of MeOH. 5% Rhodium on Alumina (240 mg) was added, and the contents were stirred under a hydrogen balloon overnight. The contents were then filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The resulting crude product was purified via reverse phase HPLC to provide [(2R)-3-(2-{5-chloro-3-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-fluorophenyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (single unknown diastereomer) (142 mg, 56%). LCMS: (M+H)+: 498.3.

Workup

  1. filtrationThe contents were then filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting crude product was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-6d8c33e75dc64fb397a526d6fa34e2a1
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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