HCID 68933671, compound → HCID 86627528, compound

HRID 1970020Notes

Reaction equation

HRID 1970020 reaction equation
[CH2:1]([C:3]([OH:5])=[O:4])[CH3:2].C([N:13]1[CH:18]2[CH2:19][CH2:20][CH:14]1[CH2:15][CH:16]([NH:21][S:22]([C:25]1[CH:34]=[CH:33][C:32]3[NH:31][C:30](=[O:35])[C:29]4[NH:36][CH:37]=[CH:38][C:28]=4[C:27]=3[CH:26]=1)(=[O:24])=[O:23])[CH2:17]2)C1C=CC=CC=1>C(O)C.[Pd]>[CH:14]12[NH:13][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]([NH:21][S:22]([C:25]1[CH:34]=[CH:33][C:32]3[NH:31][C:30](=[O:35])[C:29]4[NH:36][CH:37]=[CH:38][C:28]=4[C:27]=3[CH:26]=1)(=[O:23])=[O:24])[CH2:15]2.[CH2:1]([C:3]([O-:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 68933671HCID 68933671, compound

Product 1

HCID 86627528HCID 86627528, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4 mg of activated Pd 10% on charcoal is added to a solution of 75 mg (0.14 mmol) of 8-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate dissolved in 15 mL of ethanol. The solution is stirred under a hydrogen atmosphere at room temperature for 18 hours then filtered on celite. The filtrate is evaporated and the residue is purified by chromatography on silica (eluent dichloromethane/methanol/ammonia 200/25/4) to give 20 mg (32%) of 8-(8-aza-bicyclo[3.2.1]oct-3-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a brown solid.

Workup

  1. filtrationthen filtered on celite
  2. customThe filtrate is evaporated
  3. customthe residue is purified by chromatography on silica (eluent dichloromethane/methanol/ammonia 200/25/4)

Sources & evidence

ORD record
ord-b52684d6052841a0b3867c4df2d0e347
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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