Ethyl Acetate → HCID 22379448, compound

HRID 849430Notes

Reaction equation

HRID 849430 reaction equation
Cl.Cl.Cl.N1C=C(C[N:10]2[C:16]3[CH:17]=[CH:18][C:19](C4C=NC=CC=4)=[CH:20][C:15]=3C[N:13](C(=O)C(F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)N=C1.[H][H].C(OCC)(=[O:44])C>[OH-].[OH-].[Pd+2]>[O:44]=[C:11]1[NH:10][C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:15]=2)[NH:13][CH:12]1[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178418361HCID 178418361, compoundHCID 178478619HCID 178478619, compound

Product 1

HCID 22379448HCID 22379448, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of Compound B (720 mg, 2.34 mmol) in ethyl acetate (5 mL) at rt was added 20% Pd(OH)2 /C (40 mg). The flask was filled with hydrogen gas via a balloon. After 5 hr, the mixture was filtered through celite, and the filtrate was concentrated in vacuo. The colorless solid was chromatographed (silica, flash, 30% EtOAc/hexanes) to afford Compund C (550 mg, 98%) as a solid. MS (M+H)+ 239.

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe colorless solid was chromatographed (silica, flash, 30% EtOAc/hexanes)
  4. customto afford Compund C (550 mg, 98%) as a solid

Sources & evidence

ORD record
ord-5330d37b93b14643989cf7416402431d
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

Loading…