HCID 86636986, compound → HCID 58000637, compound

HRID 1366555Notes

Reaction equation

HRID 1366555 reaction equation
[Cl:1][C:2]1[N:7]=[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])[C:5]([F:31])=[C:4]([NH:32][CH:33]2[CH2:36][CH2:35][CH2:34]2)[N:3]=1>CO.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[N:7]=[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]([OH:16])[CH:14]=[O:15])[C:5]([F:31])=[C:4]([NH:32][CH:33]2[CH2:36][CH2:35][CH2:34]2)[N:3]=1

Participants

4

Reactant 1

HCID 86636986HCID 86636986, compound

Product 1

HCID 58000637HCID 58000637, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

[(2R)-3-{2-[2-Chloro-6-(cyclobutylamino)-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.055 g, 0.106 mmol) was dissolved in MeOH (5 mL) at room temperature. Pd(OH)2 (0.006 g) was added and the contents were stirred under a hydrogen balloon for 4 hours. The contents were filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The above procedure was repeated 3 more times. Twice Pd(OH)2 (0.010 g) was used and the third time Pd(OH)2 (0.015 g) was used and The reaction was stirred for 5.5 hours. The contents were filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The resulting crude product was purified by RP-HPLC to provide [(2R)-3-{2-[2-chloro-6-(cyclobutylamino)-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide as a tan solid (0.005 g, 11%). LCMS: (M+H)+=428.9.

Workup

  1. filtrationThe contents were filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. stirringThe reaction was stirred for 5.5 hours
  5. filtrationThe contents were filtered
  6. customto remove the catalyst
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe resulting crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-6fee70bd02a74f789f9198a521a0c54c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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