HCID 86636995, compound → HCID 58000543, compound

HRID 1366587Notes

Reaction equation

HRID 1366587 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[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:3]=1>[OH-].[OH-].[Pd+2].CO>[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[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[C:5]([F:31])=[C:4]([NH:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:3]=1

Participants

4

Reactant 1

HCID 86636995HCID 86636995, compound

Product 1

HCID 58000543HCID 58000543, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

[(2R)-3-{2-[2-Chloro-5-fluoro-6-(tetrahydro-2H-pyran-4-ylamino)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.321 g, 0.58 mmol), Pd(OH)2 (0.064 g) and MeOH (10 mL) were combined and treated as described in General Procedure E, Part D, for 4 hours. The reaction was not complete, and therefore the contents were filtered to remove the catalyst, and the filtrate was concentrated in vacuo. The resulting residue was redissolved in MeOH (10 mL), Pd(OH)2 (0.080 g) was, and the contents were again stirred under hydrogenation conditions as described in General Procedure E, Part D, for 2.5 hours. The contents were then 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-5-fluoro-6-(tetrahydro-2H-pyran-4-ylamino)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide as an off-white solid (0.024 g, 9%). LCMS: (M+H)+=459.5.

Workup

  1. additiontreated
  2. filtrationthe contents were filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe resulting residue was redissolved in MeOH (10 mL)
  6. waitas described in General Procedure E, Part D, for 2.5 hours
  7. filtrationThe contents were then filtered
  8. customto remove the catalyst
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe resulting crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-239ad1c7bda84172aa13f62b584b4ea0
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…