benzyl 5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-ylcarbamate → 1-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one

HRID 18927Notes

Reaction equation

HRID 18927 reaction equation
[C:1]([C:5]1[NH:9][C:8]([C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[NH:15][CH2:14][CH2:13]2)=[O:11])=[C:7]([NH:20]C(=O)OCC2C=CC=CC=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:20][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[NH:9][C:8]=1[C:10]([N:12]1[CH2:18][CH2:17][C:16](=[O:19])[NH:15][CH2:14][CH2:13]1)=[O:11]

Participants

4

Reactant 1

HCID 58679168benzyl 5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-ylcarbamate

Product 1

HCID 586792281-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-oneYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the previously benzyl 5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-ylcarbamate (40 mg, 0.097 mmol), Pd on charcoal (10% w/w, 20 mg) and methanol (2 mL) was shaken in a Parr shaker under hydrogen (50 psi) for 18 hours. The reaction mixture was filtered through celite and the residue was concentrated under vacuum to afford 20 mg of the desired 1-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one as a clear oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe residue was concentrated under vacuum

Sources & evidence

ORD record
ord-3660b64740ea48ad90ac0f6204b799bb
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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