HCID 86637008, compound → HCID 58000582, compound

HRID 1366620Notes

Reaction equation

HRID 1366620 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]([N:32]2[CH2:36][CH:35]([N:37]([CH3:39])[CH3:38])[CH2:34][C:33]2([CH3:41])[CH3:40])[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[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[C:5]([F:31])=[C:4]([N:32]2[CH2:36][CH:35]([N:37]([CH3:39])[CH3:38])[CH2:34][C:33]2([CH3:41])[CH3:40])[N:3]=1

Participants

4

Reactant 1

HCID 86637008HCID 86637008, compound

Product 1

HCID 58000582HCID 58000582, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (1.6493 g, 2.795 mmol) in MeOH (28 mL) was added 20% Pd(OH)2/C (50% water, 165 mg). The mixture was hydrogenated for 3.5 h, and then filtered. The solution was concentrated in vacuo, and the residue was purified by Gilson RPLC to provide [(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (0.7580 g, 54%, single unknown diastereomer) as a pink solid following crystallization from EtOAc-hexanes. LCMS: (M+H)+: 500.3.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by Gilson RPLC
  4. customto provide
  5. custom[(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (0.7580 g, 54%, single unknown diastereomer) as a pink solid following crystallization from EtOAc-hexanes

Sources & evidence

ORD record
ord-1f43bc5d22234e88a24b015e3c4af2ee
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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