Potassium Carbonate → HCID 69659718, compound

HRID 722724Notes

Reaction equation

HRID 722724 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:16]2[CH:9]([CH2:10][CH:11]=[CH:12][CH2:13][CH:14]([NH:18][C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][N:22]=3)=[O:20])[C:15]2=[O:17])[CH2:8][N:7](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:6]1)=[O:4].SC1C=CC(O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([CH:5]1[N:16]2[CH:9]([CH2:10][CH:11]=[CH:12][CH2:13][CH:14]([NH:18][C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][N:22]=3)=[O:20])[C:15]2=[O:17])[CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 69660433HCID 69660433, compound

Product 1

HCID 69659718HCID 69659718, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[(isoquinoline-1-carbonyl)-amino]-2-(2-nitro-benzenesulfonyl)-5-oxo-1,3,4,5,6,7,10,10a-octahydro-2H-2,4a-diaza-benzocyclooctene-4-carboxylic acid methyl ester (1.5 g, 2.53 mmol) in DMF (55 mL) is added 4-mercaptophenol (1.28 g, 10.1 mmol) and K2CO3 (1.4 g, 10.1 mmol). The solution is stirred at rt for 12 hrs, diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered, and concentrated. The crude residue is purified by preparative reverse phase HPLC (CH3CN/H2O with 0.1% TFA) to yield 1.16 g of product as a TFA salt.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue is purified by preparative reverse phase HPLC (CH3CN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-f045ecf12ab84e18bb508b97061c1e3d
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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