HCID 86636953, compound → HCID 58000758, compound

HRID 1366478Notes

Reaction equation

HRID 1366478 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][C@H:32]3[CH3:38])[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([O:12]CC2C=CC=CC=2)[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][C@H:32]3[CH3:38])[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86636953HCID 86636953, compound

Product 1

HCID 58000758HCID 58000758, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (15.60 g, 28.8 mmol) in methanol (115 mL) was added Pd/C (50% water, 3.1 g). The mixture was hydrogenated under balloon pressure for 2 h, and then filtered through a glass fiber filter. The solution was then concentrated in vacuo and azeotroped with EtOAc (100 mL). The resulting solid was triturated with 70% EtOAc in hexanes, and collected by vacuum filtration. The supernatant was concentrated in vacuo and crystallized from EtOAc-hexanes, and the solid was combined with the first crop of material. The combined solid was dried overnight under high vacuum to give [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide (8.15 g, 18.05 mmol, 62.7% yield) as a white solid. LCMS: (M+H)+: 451.8.

Workup

  1. filtrationfiltered through a glass fiber
  2. filtrationfilter
  3. concentrationThe solution was then concentrated in vacuo
  4. customazeotroped with EtOAc (100 mL)
  5. customThe resulting solid was triturated with 70% EtOAc in hexanes
  6. filtrationcollected by vacuum filtration
  7. concentrationThe supernatant was concentrated in vacuo
  8. customcrystallized from EtOAc-hexanes
  9. customThe combined solid was dried overnight under high vacuum

Sources & evidence

ORD record
ord-75a2c1a2509f484d82c06d1e69270597
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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