3-(4-((Benzyloxycarbonylamino)methyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate → Lx-7101

HRID 216071Notes

Reaction equation

HRID 216071 reaction equation
[CH3:1][N:2]([CH3:43])[C:3](=[O:42])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][NH:31]C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>[Pd].CO>[CH3:43][N:2]([CH3:1])[C:3](=[O:42])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][NH2:31])[CH2:15][CH2:16][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1

Participants

4

Reactant 1

HCID 579202083-(4-((Benzyloxycarbonylamino)methyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

Product 1

HCID 56962369Lx-7101Yield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-((Benzyloxycarbonylamino)methyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate (0.140 g, 0.239 mmol) from example 19, step E, Pd/C (10% Pd/C, Pearlman), and methanol (5 mL) were combined and hydrogenated overnight at 1 atmosphere. The reaction was filtered through celite, concentrated under vacuum, and purified by neutral phase prep-HPLC to give the title compound as the acetate salt in 52% yield.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated under vacuum
  3. custompurified by neutral phase prep-HPLC

Sources & evidence

ORD record
ord-75b179796244493eb282369f0887be86
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

Loading…