HCID 44482113, compound → HCID 57920197, compound

HRID 216057Notes

Reaction equation

HRID 216057 reaction equation
[CH3:1][N:2]([CH3:40])[C:3](=[O:39])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][O:31]CC3C=CC=CC=3)[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>C1COCC1.[Pd]>[CH3:40][N:2]([CH3:1])[C:3](=[O:39])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:30][OH: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 44482113HCID 44482113, compound

Product 1

HCID 57920197HCID 57920197, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-(benzyloxymethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate from example 15, step E, (30 mg, 0.055 mmol) in THF (2 mL) was added Pd/C (10%). The reaction mixture was stirred under H2 at 60 psi overnight. The mixture was filtered and concentrated under vacuum. The residue was purified by prep HPLC (30×250 mm C18 column, 10-100% MeCN:H2O (10 mM NH4OAc), 18 min, 45 mL/min) to give the title compound (1 mg).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by prep HPLC (30×250 mm C18 column, 10-100% MeCN:H2O (10 mM NH4OAc), 18 min, 45 mL/min)

Sources & evidence

ORD record
ord-14b05460b16149d98c2fb4c350044a7a
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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