HCID 86636968, compound → HCID 58000696, compound

HRID 1366510Notes

Reaction equation

HRID 1366510 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[CH2:37][CH:36]([N:38]([CH3:40])[CH3:39])[C:33]4([CH2:35][CH2:34]4)[CH2:32]3)[N:27]=[C:26]([CH2:41][CH3:42])[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[CH2:37][CH:36]([N:38]([CH3:40])[CH3:39])[C:33]4([CH2:35][CH2:34]4)[CH2:32]3)[N:27]=[C:26]([CH2:41][CH3:42])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86636968HCID 86636968, compound

Product 1

HCID 58000696HCID 58000696, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-ethyl-5-fluoro-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1058 g, 0.182 mmol) in MeOH (5 mL) was added 10% Pd/C (50% water, 32 mg). The mixture was hydrogenated under balloon pressure for 1 h, and then filtered. The solution was concentrated in vacuo, and the residue was azeotroped with EtOAc and crystallized from EtOAc-hexanes to afford [(2R)-2-(cyclopentylmethyl)-3-(2-{6-[7-(dimethylamino)-5-azaspiro[2.4]hept-5-yl]-2-ethyl-5-fluoro-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide (0.0795 g, 89% yield, mixture of diastereomers) as a white solid. LCMS: (M+H)+: 492.3.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was azeotroped with EtOAc
  4. customcrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-b9a9d83cff5b40ed893cd581cb06680d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…